WO2009086064A1 - Method for preparing a moisture curable hot melt adhesive - Google Patents
Method for preparing a moisture curable hot melt adhesive Download PDFInfo
- Publication number
- WO2009086064A1 WO2009086064A1 PCT/US2008/087615 US2008087615W WO2009086064A1 WO 2009086064 A1 WO2009086064 A1 WO 2009086064A1 US 2008087615 W US2008087615 W US 2008087615W WO 2009086064 A1 WO2009086064 A1 WO 2009086064A1
- Authority
- WO
- WIPO (PCT)
- Prior art keywords
- hot melt
- chain extender
- isocyanate
- melt adhesive
- mixture
- Prior art date
Links
Classifications
-
- 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
-
- 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
- C08G18/08—Processes
- C08G18/10—Prepolymer processes involving reaction of isocyanates or isothiocyanates with compounds having active hydrogen in a first reaction step
- C08G18/12—Prepolymer processes involving reaction of isocyanates or isothiocyanates with compounds having active hydrogen in a first reaction step using two or more compounds having active hydrogen in the first polymerisation step
-
- 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
- C08G2170/00—Compositions for adhesives
- C08G2170/20—Compositions for hot melt adhesives
Definitions
- Hot melt adhesives are solid at room temperature but, upon application of heat, melt to a liquid or fluid state in which form they are applied to a substrate On cooling, the adhesive regains its solid form The hard phase(s) formed upon cooling the adhesive imparts all of the cohesion (strength, toughness, creep and heat resistance) to the final adhesive Curable hot melt adhesives, which are also applied in molten form, cool to solidify and subsequently cure by a chemical crosslinking reaction
- An advantage of hot melt curable adhesives over traditional liquid curing adhesives is their ability to provide "green strength" upon cooling prior to cure
- Advantages of hot melt curable adhesives over non-curing hot melt adhesives include improved temperature and chemical resistance
- the majority of reactive hot melts are moisture-curing urethane adhesives These adhesives consist primarily of isocyanate terminated polyurethane prepolymers that react with surface or ambient moisture in order to chain-extend, forming a new polyurethane/urea polymer
- Polyurethane prepolymers are conventionally obtained by reacting polyols with isocyanates
- Additives are commonly included in reactive hot melt adhesive formulations to provide improved properties, such as improved green strength before solidification and increased cure speed Cure is obtained through the diffusion of moisture from the atmosphere or the substrate into the adhesive and subsequent reaction
- the reaction of moisture with residual isocyanate forms carbamic acid This acid is unstable, decomposing into an amine and carbon dioxide
- the amine reacts rapidly with isocyanate to form a urea
- the final adhesive product is a crosslinked material polymerized primarily through urea groups and urethane groups
- Moisture curing adhesives are generally prepared in a one-step polymerization method While two step-polymerization method are know in the art, such as the processes disclosed in U S Patent No 6,365,700 and U S Patent No 7,074,297, there continues to be a need in the art for novel polymerization manufacturing processes for forming moisture reactive hot melt adhesives The present invention addresses this need SUMMARY OF THE INVENTION
- the current invention provides a novel process to make high green strength moisture reactive hot melt adhesives It has been discovered that adding chain extenders in a second step after the main polyol/MDI reaction results in moisture curable hot melt adhesives having improved green strength
- Still another embodiment of the invention is directed to a method for bonding materials together which comprises applying the moisture reactive hot melt adhesive composition of the invention in a liquid form to a first substrate, bringing a second substrate in contact with the composition applied to the first substrate, and subjecting the applied composition to conditions which will allow the composition to cool and cure to an irreversible solid form, said conditions comprising moisture
- FIG 1 illustrates diagrammatically the polymerization process of the invention
- Figure 2 compares the green strength of adhesives having the same compositional formulation, made with the process of the invention and the conventional one-step process
- Moisture curing hot melt adhesives consist primarily of isocyanate-capped polyurethane prepolymers obtained by reacting diols (typically polyethers, polyesters and polybutadienes) with a polyisocyanate (most commonly methylene bisphenyl diisocyanate (MDI))
- MDI methylene bisphenyl diisocyanate
- a moisture curable hot melt adhesive is prepared by ( ⁇ ) forming a mixture comprising an isocyanate prepolymer and excess isocyanate and then (n) adding to the reaction product formed in step (i) a chain extender to form an isocyanate terminated moisture curable hot melt adhesive
- the mixture formed in step (i) can be prepared by reacting excess isocyanate with an active hydrogen-containing compound
- Active hydrogen-containing compounds include -OH (hydroxyl) group containing compounds such as polyols or hydroxyl containing chain extenders, -NH (amino) group containing compounds such as diamino or t ⁇ amino polypropylene glycol or diamino or t ⁇ amino polyethylene glycol, -SH (mercapto) group containing compounds such as polythiols, and -COOH (carboxyl) group containing compounds Included are hydroxyl, amino, mercapto, and carboxyl- containmg tackifiers or thermoplastic polymers
- a mixture comprising an isocyanate prepolymer and excess isocyanate is prepared by reacting excess isocyanate with a polyol
- a polyol is reacted with excess isocyanate (e g , MDI) in the first step
- a moisture curable hot melt adhesive is formed by reacting excess isocyanate with polyol to form a mixture comprising isocyanate terminated prepolymer and excess isocyanate To this mixture is then added a chain extender to form an isocyanate terminated polyurethane hot melt adhesive
- chain extenders used in the practice of the invention are well known to those skilled in the polyurethane field
- Non-limiting examples of useful chain extenders include polyol chain extenders such as ethylene glycol, 1 ,4-butane diol, 1 ,6-hexane diol, 1 ,4-b ⁇ s(hydroxymethyl)cyclohexane (CHDM), p-d ⁇ (2- hydroxyethoxy)benzene (HQEE), m-d ⁇ (2-hydroxyethoxy)benzene (HER), trimethylolpropane (TMP), and low molecular weight polyether polyols, and polyamine chain extenders
- the urethane adhesive formed by this novel process exhibits improved green strength compared to formulation having the same composition but made from the conventional one-step process
- the cured adhesive exhibits improved tensile properties including high elasticity
- This new method provides a simple yet novel and unique way to achieve a high green strength reactive hot melt adhesive, which cures into a highly elastic material
- the adhesives of the invention comprise an isocyanate component
- useful isocyanate components include methyenebisphenyldiisocyanate (MDI), isophoronediisocyanate (IPDI), hydrogenated methylenebisphenyldiisocyanate (HMDI) and toluene diisocyanate (TDI)
- MDI methyenebisphenyldiisocyanate
- IPDI isophoronediisocyanate
- HMDI hydrogenated methylenebisphenyldiisocyanate
- TDI toluene diisocyanate
- the isocyanate component is typically used in amounts of from about 5 to about
- the adhesive will also contain an active hydrogen-containing compound such as a polyol
- Non-limiting examples include polyether polyols, polyester polyols and polybutadienes
- the added polyol will typically be used in amounts of from about from about 0 01 to about 90 wt %
- thermoplastic resins such as thermoplastic resins, (meth)acryl ⁇ c polymers, and functionally modified polyolefin
- polymers may be blended with the polyol prior to reaction thereof with the isocyanate, or may be added to the isocyanate terminated prepolymer
- the reactive hot melt compositions of the invention are useful in the manufacture of articles made of a wide variety of substrates (materials), including but not limited to wood, metal, polymeric plastics, glass and textiles
- the adhesives find use in manufacture of consumer products and in specialized industrial applications Markets where the adhesives find use includes textiles (e g , carpet and clothing), food packaging, footwear, consumer, construction, furniture, automotive and aircraft Applications include but are not limited to use in water towers, for bonding to exterior surfaces, bonding to wood with high levels of pitch and e g , in marine and automotive applications, use as a glazing/backbedding compound in the manufacture of windows, use in the manufacture of doors including entry doors, garage doors and the like, use in the manufacture of architectural panels, use in bonding components on the exterior of vehicles, use in the manufacture of flooring and the like
- Any suitable compound, which contains two or more isocyanate groups, may be used for preparing the urethane prepolymers
- Organic polyisocyanates which may be used to practice the invention, include alkylene diisocyanates, cycloalkylene dnsocyanates, aromatic diisocyanates and aliphatic-aromatic diisocyanates
- suitable isocyanate-containing compounds include, but are not limited to, ethylene dnsocyanate, ethylidene dnsocyanate, propylene dnsocyanate, butylene diisocyanate, t ⁇ methylene dnsocyanate, hexamethylene dnsocyanate, toluene dnsocyanate, cyclopentylene-1 , 3-d ⁇ socyanate, cyclo-hexylene-1 ,4-d ⁇ socyanate, cyclohexylene-1 ,2-d ⁇ socyanate, 4,4'-d ⁇ phenylmethane dnsocyanate, 2,2-d ⁇ phenylpropane-4,4'-d ⁇
- the prepolymer is most commonly prepared by the polymerization of a polyisocyanate with a polyol, most preferably the polymerization of a diisocyanate with a low molecular weight diol
- Polyols useful in the practice of the invention include polyhydroxy ethers (substituted or unsubstituted polyalkylene ether glycols or polyhydroxy polyalkylene ethers), the ethylene or propylene oxide adducts of polyols and the monosubstituted esters of glycerol, polyamide polyols, acrylic polyols, crystalline, amorphous and/or liquid polyesters, castor oil and vegetable oils of different molecular weight and functionality, other fatty polyols, polybutadiene diol, polyisobutylene diol as well as mixtures thereof
- polyether polyols include a linear and/or branched polyether having hydroxyl groups, and contain substantially no functional group other than the hydroxyl groups
- the polyether polyol may include polyoxyalkylene polyol such as polyethylene glycol, polypropylene glycol, polybutylene glycol and the like Further, a homopolymer and a copolymer of the polyoxyalkylene polyols may also be employed Particularly preferable copolymers of the polyoxyalkylene polyols may include an adduct at least one compound selected from the group consisting of ethylene glycol, propylene glycol, diethylene glycol, dipropylene glycol, t ⁇ ethylene glycol, 2-ethylhexaned ⁇ ol-1 , 3, glycerin, 1 ,2,6-hexane triol, t ⁇ methylol propane, t ⁇ methylol ethane, t ⁇ s(hydroxyphenyl)propane, triethanolamine, trns
- polystyrene resin such as ARCOL PPG 2025 (Bayer), PoIyG 20-56 (Arch) and PoIyG 30-42 (Arch), polyamide polyols such as PAPOL polyol (Arizona Chemical), crystalline polyesters such as LEXOREZ 1 130-30P, LEXOREZ 1 150-30P and LEXOREZ 1 151-35P from the LEXOREZ series from Inolex Chemical Co DYNACOLL 7360, DYNACOLL 7361 series of resins available from Degussa, and FORMREZ 66-20 from Witco Chemical Company, poly- ⁇ -caprolactones that are useful in the invention include the CAPA® series polyols from Solvay, amorphous or liquid polyesters such as Dynacoll 7230 (Degussa) and Stepanpol PD-56 (Stepan), and polybutadiene such as PoIyBD R- 45HTLO (Sartomer) "Polymer
- fatty polyols may include castor oil, the products of hydroxylation of unsaturated or polyunsaturated natural oils, the products of hydrogenations of unsaturated or polyunsaturated polyhydroxyl natural oils, polyhydroxyl esters of alkyl hydroxyl fatty acids, polymerized natural oils, soybean polyol and alkylhydroxylated amides of fatty acids
- the adhesive may optionally contain a thermoplastic polymer
- the thermoplastic polymer may be either a functional or a non-functional thermoplastic
- suitable thermoplastic polymers include acrylic polymers, functional acrylic polymers, non-functional acrylic polymers, acrylic block copolymer, acrylic polymer having tertiary-alkyl amide functionality, polysiloxane polymers, polystyrene copolymers, polyvinyl polymers, divinylbenzene copolymers, polyetheramides, polyvinyl acetal, polyvinyl butyral, polyvinyl acetate, polyvinyl chloride, methylene polyvinyl ether, cellulose acetate, styrene acrylonit ⁇ le, amorphous polyolefin, olefin block copolymer [OBC], polyolefin plastomer, thermoplastic urethane, polyacrylonit ⁇ le, ethylene vinyl acetate copolymer, ethylene vinyl acetate terpolymers
- thermoplastic polymers are commercially available Non-limiting examples include ethylene vinyl acetate copolymers such as the Elvax® EVA resins (DuPont), ethylene acrylate copolymers such as the EnableTM resins (ExxonMobil), and (meth)acryl ⁇ c polymers such as the Elvacite® resins (Lucite) and Degalan resins (Degussa)
- the adhesive may also optionally contain a functionally modified polyolefin
- a particularly useful functionally modified polyolefin is oxidized polyethylene
- the number average molecular weight of the functionally modified polyolefins is in the range of about 50 to 100,000, more preferably about 100 to 10,000
- Non-limiting examples include EE-2 polymer, which is commercially available from Westlake Chemical, and the EPOLENE® series, available from Eastman Chemical Company
- the adhesives may also, if desired, be formulated with other conventional additives which are compatible with the composition
- additives include defoamers, plasticizers, compatible tackifiers, curing catalysts, dissociation catalysts, fillers, rheology modifiers, antioxidants, pigments, adhesion promoters, stabilizers, aliphatic C 5 -C 10 terpene oligomers, bituminous materials and the like
- Thixotropic agents such as fumed silica, may also be added to provide sag resistance
- Conventional additives that are compatible with a composition according to this invention may simply be determined by combining a potential additive with the composition and determining if they are compatible An additive is compatible if it is homogenous within the product
- suitable additives include, without limitation, rosin, rosin derivatives, rosin ester, aliphatic hydrocarbons, aromatic hydrocarbons, aromatically modified aliphatic hydrocarbons, terpenes, terpene phenol, modified
- the invention also provides a method for bonding articles together which comprises applying the reactive hot melt adhesive composition of the invention in a liquid melt form to a first article, bringing a second article in contact with the composition applied to the first article, and subjecting the applied composition to conditions which will allow the composition to cool and cure to a composition having an irreversible solid form, said conditions comprising moisture
- the composition is typically distributed and stored in its solid form, and is stored in the absence of moisture When the composition is ready for use, the solid is heated and melted prior to application
- this invention includes reactive polyurethane hot melt adhesive compositions in both its solid form, as it is typically to be stored and distributed, and its liquid form, after it has been melted, just prior to its application
- the reactive hot melt adhesive composition After application, to adhere articles together, the reactive hot melt adhesive composition is subjected to conditions that will allow it to solidify and cure to a composition that has an irreversible solid form Solidification (setting) occurs when the liquid melt begins to cool from its application temperature to room temperature Curing, i e chain extending, to a composition that has an irreversible solid form, takes place in the presence of ambient moisture
- Solidification occurs when the liquid melt begins to cool from its application temperature to room temperature
- Adhesive batch sample 1 prepared in accordance with example 1 using the conventional single step polymerization
- adhesive batch sample 2 prepared in accordance with example 2 using the two-step process of the invention
- the formulations prepared using the two-step polymerization process of the invention had improved green strength and set speed as compared with the same formulation prepared using a conventional one-step polymerization method
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Adhesives Or Adhesive Processes (AREA)
- Polyurethanes Or Polyureas (AREA)
Abstract
Description
Claims
Priority Applications (4)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
JP2010539858A JP5877945B2 (en) | 2007-12-21 | 2008-12-19 | Method for producing a moisture curable hot melt adhesive |
CN2008801254474A CN101977953A (en) | 2007-12-21 | 2008-12-19 | Method for preparing a moisture curable hot melt adhesive |
EP08866094A EP2231739A1 (en) | 2007-12-21 | 2008-12-19 | Method for preparing a moisture curable hot melt adhesive |
BRPI0821640-1A BRPI0821640A2 (en) | 2007-12-21 | 2008-12-19 | Method for forming a moisture-curable heat-melt adhesive, moisture-curable heat-melt adhesive, material bonding method, an article manufacturing process, and an article of manufacture |
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US11/962,872 US8574394B2 (en) | 2007-12-21 | 2007-12-21 | Method for preparing a moisture curable hot melt adhesive |
US11/962,872 | 2007-12-21 |
Publications (1)
Publication Number | Publication Date |
---|---|
WO2009086064A1 true WO2009086064A1 (en) | 2009-07-09 |
Family
ID=40551026
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
PCT/US2008/087615 WO2009086064A1 (en) | 2007-12-21 | 2008-12-19 | Method for preparing a moisture curable hot melt adhesive |
Country Status (6)
Country | Link |
---|---|
US (1) | US8574394B2 (en) |
EP (1) | EP2231739A1 (en) |
JP (1) | JP5877945B2 (en) |
CN (1) | CN101977953A (en) |
BR (1) | BRPI0821640A2 (en) |
WO (1) | WO2009086064A1 (en) |
Cited By (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN102079961A (en) * | 2010-11-21 | 2011-06-01 | 乐凯集团第二胶片厂 | Ultraviolet curing adhesive |
CN104371631A (en) * | 2014-12-05 | 2015-02-25 | 浙江多邦化工有限公司 | Single-component solvent-free moisture-cured polyurethane adhesive and preparing method thereof |
Families Citing this family (12)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
TWI362394B (en) * | 2007-02-12 | 2012-04-21 | Univ Tamkang | Preparing method for reactive hydrophilic polyurethane resins and their applications at ambient temperature |
US20140262189A1 (en) * | 2008-01-25 | 2014-09-18 | Henkel US IP LLC | Curable compositions and fluid connections made therewith |
JP5642047B2 (en) | 2010-12-21 | 2014-12-17 | ローム アンド ハース カンパニーRohm And Haas Company | Adhesive composition |
JP2013116993A (en) * | 2011-12-05 | 2013-06-13 | Henkel Japan Ltd | Moisture-curable hot melt adhesive |
CN104356994B (en) * | 2014-10-23 | 2016-02-17 | 招远鸿瑞印染有限公司 | A kind of methyl isocyanate hot melt material |
CN104886171A (en) * | 2015-05-11 | 2015-09-09 | 浙江美华鼎昌医药科技有限公司 | Polyurethane mosquito-repellent tablet and preparation method thereof |
JP5996080B1 (en) | 2015-12-16 | 2016-09-21 | ショーワグローブ株式会社 | GLOVE WITH ARM COVER AND METHOD FOR PRODUCING GLOVE WITH ARM COVER |
CN109206569B (en) * | 2017-07-03 | 2021-01-19 | 比亚迪股份有限公司 | Waterborne polyurethane, waterborne polyurethane adhesive and preparation method thereof |
CN107236512A (en) * | 2017-07-19 | 2017-10-10 | 东莞市联洲知识产权运营管理有限公司 | A kind of preparation method for the moisture-curable polyurethane hot melt that kaolin refractory fiber is modified |
EP3794051A4 (en) * | 2018-05-18 | 2022-01-05 | Henkel AG & Co. KGaA | Stable and low cure-temperature 1k polyisocyanate |
US11795355B2 (en) * | 2018-08-24 | 2023-10-24 | Ddp Specialty Electronic Materials Us, Llc | One-component hot melt polyurethane adhesive |
JP7140661B2 (en) | 2018-12-04 | 2022-09-21 | 株式会社プロスパイラ | strut mount |
Citations (4)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US4719278A (en) * | 1986-03-29 | 1988-01-12 | Bayer Aktiengesellschaft | Process for the preparation of thixotropic binders, the binder obtainable by this process and their use for the preparation of coating and sealing compounds |
US4778845A (en) * | 1986-08-04 | 1988-10-18 | Sika Ag, Vorm. Kaspar Winkler & Co. | One-part adhesive and/or sealing mass which is stable and pumpable at temperatures up to 30 degree C. |
GB2427610A (en) * | 2005-06-16 | 2007-01-03 | Mcp Ind Inc | An adhesive polyurethane composition |
EP1811006A1 (en) * | 2006-01-23 | 2007-07-25 | Purbond AG | Adhesive system |
Family Cites Families (8)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US5869593A (en) * | 1991-07-01 | 1999-02-09 | H. B. Fuller Licensing & Financing, Inc. | High moisture vapor transmission hot melt moisture cure polyurethane adhesive |
DE19908561A1 (en) * | 1998-03-26 | 1999-09-30 | Henkel Kgaa | Adhesive pencil with high tack and good setting and strength properties etc., useful for bonding paper or as general-purpose adhesive |
JP2005511873A (en) * | 2001-12-18 | 2005-04-28 | ヘンケル・コマンディットゲゼルシャフト・アウフ・アクチエン | Method for producing polyurethane-prepolymer with low monomer content |
GB0207345D0 (en) * | 2002-03-28 | 2002-05-08 | Unichema Chemie Bv | Polyurethane |
JP4073246B2 (en) * | 2002-05-10 | 2008-04-09 | 横浜ゴム株式会社 | Polyurethane ionomer and method for producing the same |
US20040087754A1 (en) * | 2002-10-31 | 2004-05-06 | Paul Foley | Polyurethane compounds and articles prepared therefrom |
WO2007061446A1 (en) * | 2005-11-22 | 2007-05-31 | Invista Technologies S.A.R.L. | Spandex from high molecular weight poly (tetramethylene-co-ethyleneether) glycols |
KR100790849B1 (en) * | 2006-01-27 | 2008-01-02 | 삼성에스디아이 주식회사 | Polyurethane binder, electrodes containing the same and the lithium battery containing the electrodes |
-
2007
- 2007-12-21 US US11/962,872 patent/US8574394B2/en not_active Expired - Fee Related
-
2008
- 2008-12-19 JP JP2010539858A patent/JP5877945B2/en not_active Expired - Fee Related
- 2008-12-19 BR BRPI0821640-1A patent/BRPI0821640A2/en not_active IP Right Cessation
- 2008-12-19 CN CN2008801254474A patent/CN101977953A/en active Pending
- 2008-12-19 WO PCT/US2008/087615 patent/WO2009086064A1/en active Application Filing
- 2008-12-19 EP EP08866094A patent/EP2231739A1/en not_active Withdrawn
Patent Citations (4)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US4719278A (en) * | 1986-03-29 | 1988-01-12 | Bayer Aktiengesellschaft | Process for the preparation of thixotropic binders, the binder obtainable by this process and their use for the preparation of coating and sealing compounds |
US4778845A (en) * | 1986-08-04 | 1988-10-18 | Sika Ag, Vorm. Kaspar Winkler & Co. | One-part adhesive and/or sealing mass which is stable and pumpable at temperatures up to 30 degree C. |
GB2427610A (en) * | 2005-06-16 | 2007-01-03 | Mcp Ind Inc | An adhesive polyurethane composition |
EP1811006A1 (en) * | 2006-01-23 | 2007-07-25 | Purbond AG | Adhesive system |
Cited By (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN102079961A (en) * | 2010-11-21 | 2011-06-01 | 乐凯集团第二胶片厂 | Ultraviolet curing adhesive |
CN104371631A (en) * | 2014-12-05 | 2015-02-25 | 浙江多邦化工有限公司 | Single-component solvent-free moisture-cured polyurethane adhesive and preparing method thereof |
Also Published As
Publication number | Publication date |
---|---|
EP2231739A1 (en) | 2010-09-29 |
BRPI0821640A2 (en) | 2015-06-16 |
US8574394B2 (en) | 2013-11-05 |
US20090159205A1 (en) | 2009-06-25 |
JP2011508025A (en) | 2011-03-10 |
CN101977953A (en) | 2011-02-16 |
JP5877945B2 (en) | 2016-03-08 |
Similar Documents
Publication | Publication Date | Title |
---|---|---|
US8574394B2 (en) | Method for preparing a moisture curable hot melt adhesive | |
EP2274356B1 (en) | High heat resistant adhesive and sealant compositions | |
US7625963B2 (en) | Reactive hot melt adhesive with bituminous additive | |
US20140231008A1 (en) | Moisture curable hot melt adhesive | |
EP2356189B1 (en) | Reactive hot melt adhesive | |
EP1036103B2 (en) | Modified polyurethane hotmelt adhesive | |
EP2547744B1 (en) | Silane moisture curable hot melts | |
EP1727845A1 (en) | Novel reactive hot melt adhesives | |
EP3684873B1 (en) | A high strength long open time polyurethane reactive hot melt | |
US20220235249A1 (en) | Polyurethane Hot Melt Adhesive for Low Temperature Application | |
US8664330B2 (en) | Reactive hot melt adhesive with improved hydrolysis resistance | |
WO2001049802A1 (en) | Polyurethane reactive hot melt adhesive composition | |
MXPA00005337A (en) | Modified polyurethane hotmelt adhesive | |
JPH07228855A (en) | Reactive hot-melt type adhesive |
Legal Events
Date | Code | Title | Description |
---|---|---|---|
WWE | Wipo information: entry into national phase |
Ref document number: 200880125447.4 Country of ref document: CN |
|
121 | Ep: the epo has been informed by wipo that ep was designated in this application |
Ref document number: 08866094 Country of ref document: EP Kind code of ref document: A1 |
|
WWE | Wipo information: entry into national phase |
Ref document number: 2010539858 Country of ref document: JP |
|
NENP | Non-entry into the national phase |
Ref country code: DE |
|
WWE | Wipo information: entry into national phase |
Ref document number: 2008866094 Country of ref document: EP |
|
ENP | Entry into the national phase |
Ref document number: PI0821640 Country of ref document: BR Kind code of ref document: A2 Effective date: 20100621 |