CA1192341A - Adhesive composition and composite made therewith - Google Patents
Adhesive composition and composite made therewithInfo
- Publication number
- CA1192341A CA1192341A CA000403884A CA403884A CA1192341A CA 1192341 A CA1192341 A CA 1192341A CA 000403884 A CA000403884 A CA 000403884A CA 403884 A CA403884 A CA 403884A CA 1192341 A CA1192341 A CA 1192341A
- Authority
- CA
- Canada
- Prior art keywords
- adhesive
- triol
- mixture
- weight
- phenylene diamine
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired
Links
- 239000000853 adhesive Substances 0.000 title claims abstract description 76
- 230000001070 adhesive effect Effects 0.000 title claims abstract description 76
- 239000000203 mixture Substances 0.000 title claims abstract description 38
- 239000002131 composite material Substances 0.000 title description 2
- XSTXAVWGXDQKEL-UHFFFAOYSA-N Trichloroethylene Chemical compound ClC=C(Cl)Cl XSTXAVWGXDQKEL-UHFFFAOYSA-N 0.000 claims abstract description 36
- 229920000728 polyester Polymers 0.000 claims abstract description 25
- 239000004721 Polyphenylene oxide Substances 0.000 claims abstract description 24
- 229920000570 polyether Polymers 0.000 claims abstract description 24
- CBCKQZAAMUWICA-UHFFFAOYSA-N 1,4-phenylenediamine Chemical compound NC1=CC=C(N)C=C1 CBCKQZAAMUWICA-UHFFFAOYSA-N 0.000 claims abstract description 15
- 239000003054 catalyst Substances 0.000 claims abstract description 14
- 150000003606 tin compounds Chemical class 0.000 claims abstract description 13
- GEYOCULIXLDCMW-UHFFFAOYSA-N 1,2-phenylenediamine Chemical compound NC1=CC=CC=C1N GEYOCULIXLDCMW-UHFFFAOYSA-N 0.000 claims abstract description 12
- 239000011152 fibreglass Substances 0.000 claims abstract description 3
- 229920005862 polyol Polymers 0.000 claims description 10
- 239000011541 reaction mixture Substances 0.000 claims description 10
- 239000000945 filler Substances 0.000 claims description 8
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 8
- 150000003077 polyols Chemical class 0.000 claims description 8
- 239000007795 chemical reaction product Substances 0.000 claims description 5
- IQPQWNKOIGAROB-UHFFFAOYSA-N isocyanate group Chemical group [N-]=C=O IQPQWNKOIGAROB-UHFFFAOYSA-N 0.000 claims description 5
- UKLDJPRMSDWDSL-UHFFFAOYSA-L [dibutyl(dodecanoyloxy)stannyl] dodecanoate Chemical group CCCCCCCCCCCC(=O)O[Sn](CCCC)(CCCC)OC(=O)CCCCCCCCCCC UKLDJPRMSDWDSL-UHFFFAOYSA-L 0.000 claims description 4
- 239000012975 dibutyltin dilaurate Substances 0.000 claims description 4
- 150000004985 diamines Chemical class 0.000 claims description 3
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims description 3
- 150000002148 esters Chemical class 0.000 claims 1
- 239000004848 polyfunctional curative Substances 0.000 abstract description 15
- 239000000306 component Substances 0.000 description 43
- 229920002176 Pluracol® Polymers 0.000 description 7
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 6
- WERYXYBDKMZEQL-UHFFFAOYSA-N butane-1,4-diol Chemical compound OCCCCO WERYXYBDKMZEQL-UHFFFAOYSA-N 0.000 description 6
- 239000012948 isocyanate Substances 0.000 description 6
- 239000000463 material Substances 0.000 description 6
- GOOHAUXETOMSMM-UHFFFAOYSA-N Propylene oxide Chemical compound CC1CO1 GOOHAUXETOMSMM-UHFFFAOYSA-N 0.000 description 4
- 238000006243 chemical reaction Methods 0.000 description 4
- 125000005442 diisocyanate group Chemical group 0.000 description 4
- 150000002513 isocyanates Chemical class 0.000 description 4
- -1 nitrogen contain-ing polyol Chemical class 0.000 description 4
- 239000000126 substance Substances 0.000 description 4
- 150000004072 triols Chemical class 0.000 description 4
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
- DJOWTWWHMWQATC-KYHIUUMWSA-N Karpoxanthin Natural products CC(=C/C=C/C=C(C)/C=C/C=C(C)/C=C/C1(O)C(C)(C)CC(O)CC1(C)O)C=CC=C(/C)C=CC2=C(C)CC(O)CC2(C)C DJOWTWWHMWQATC-KYHIUUMWSA-N 0.000 description 3
- 235000019738 Limestone Nutrition 0.000 description 3
- ZJCCRDAZUWHFQH-UHFFFAOYSA-N Trimethylolpropane Chemical compound CCC(CO)(CO)CO ZJCCRDAZUWHFQH-UHFFFAOYSA-N 0.000 description 3
- 238000009472 formulation Methods 0.000 description 3
- 229910052751 metal Inorganic materials 0.000 description 3
- 239000002184 metal Substances 0.000 description 3
- 238000000034 method Methods 0.000 description 3
- 229920001228 polyisocyanate Polymers 0.000 description 3
- 239000005056 polyisocyanate Substances 0.000 description 3
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 3
- ZWVMLYRJXORSEP-UHFFFAOYSA-N 1,2,6-Hexanetriol Chemical compound OCCCCC(O)CO ZWVMLYRJXORSEP-UHFFFAOYSA-N 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- 239000004215 Carbon black (E152) Substances 0.000 description 2
- 125000003277 amino group Chemical group 0.000 description 2
- 238000009835 boiling Methods 0.000 description 2
- 229930195733 hydrocarbon Natural products 0.000 description 2
- 150000002430 hydrocarbons Chemical class 0.000 description 2
- 239000004615 ingredient Substances 0.000 description 2
- 239000006028 limestone Substances 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- 239000004814 polyurethane Substances 0.000 description 2
- 229920002635 polyurethane Polymers 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- ZBBLRPRYYSJUCZ-GRHBHMESSA-L (z)-but-2-enedioate;dibutyltin(2+) Chemical compound [O-]C(=O)\C=C/C([O-])=O.CCCC[Sn+2]CCCC ZBBLRPRYYSJUCZ-GRHBHMESSA-L 0.000 description 1
- VGHSXKTVMPXHNG-UHFFFAOYSA-N 1,3-diisocyanatobenzene Chemical compound O=C=NC1=CC=CC(N=C=O)=C1 VGHSXKTVMPXHNG-UHFFFAOYSA-N 0.000 description 1
- UPMLOUAZCHDJJD-UHFFFAOYSA-N 4,4'-Diphenylmethane Diisocyanate Chemical compound C1=CC(N=C=O)=CC=C1CC1=CC=C(N=C=O)C=C1 UPMLOUAZCHDJJD-UHFFFAOYSA-N 0.000 description 1
- JOYRKODLDBILNP-UHFFFAOYSA-N Ethyl urethane Chemical compound CCOC(N)=O JOYRKODLDBILNP-UHFFFAOYSA-N 0.000 description 1
- LGRFSURHDFAFJT-UHFFFAOYSA-N Phthalic anhydride Natural products C1=CC=C2C(=O)OC(=O)C2=C1 LGRFSURHDFAFJT-UHFFFAOYSA-N 0.000 description 1
- ATJFFYVFTNAWJD-UHFFFAOYSA-N Tin Chemical compound [Sn] ATJFFYVFTNAWJD-UHFFFAOYSA-N 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 150000008064 anhydrides Chemical class 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- JHIWVOJDXOSYLW-UHFFFAOYSA-N butyl 2,2-difluorocyclopropane-1-carboxylate Chemical compound CCCCOC(=O)C1CC1(F)F JHIWVOJDXOSYLW-UHFFFAOYSA-N 0.000 description 1
- 239000006229 carbon black Substances 0.000 description 1
- 239000010960 cold rolled steel Substances 0.000 description 1
- 239000003086 colorant Substances 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 239000007859 condensation product Substances 0.000 description 1
- AYOHIQLKSOJJQH-UHFFFAOYSA-N dibutyltin Chemical compound CCCC[Sn]CCCC AYOHIQLKSOJJQH-UHFFFAOYSA-N 0.000 description 1
- 150000002009 diols Chemical class 0.000 description 1
- 125000001475 halogen functional group Chemical group 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- TZMQHOJDDMFGQX-UHFFFAOYSA-N hexane-1,1,1-triol Chemical compound CCCCCC(O)(O)O TZMQHOJDDMFGQX-UHFFFAOYSA-N 0.000 description 1
- ZADYMNAVLSWLEQ-UHFFFAOYSA-N magnesium;oxygen(2-);silicon(4+) Chemical compound [O-2].[O-2].[O-2].[Mg+2].[Si+4] ZADYMNAVLSWLEQ-UHFFFAOYSA-N 0.000 description 1
- QSHDDOUJBYECFT-UHFFFAOYSA-N mercury Chemical compound [Hg] QSHDDOUJBYECFT-UHFFFAOYSA-N 0.000 description 1
- 229910052753 mercury Inorganic materials 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- WXZMFSXDPGVJKK-UHFFFAOYSA-N pentaerythritol Chemical compound OCC(CO)(CO)CO WXZMFSXDPGVJKK-UHFFFAOYSA-N 0.000 description 1
- 229920006149 polyester-amide block copolymer Polymers 0.000 description 1
- 229920000642 polymer Polymers 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 239000001044 red dye Substances 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 150000005846 sugar alcohols Polymers 0.000 description 1
- 238000010998 test method Methods 0.000 description 1
- 239000010409 thin film Substances 0.000 description 1
- DVKJHBMWWAPEIU-UHFFFAOYSA-N toluene 2,4-diisocyanate Chemical compound CC1=CC=C(N=C=O)C=C1N=C=O DVKJHBMWWAPEIU-UHFFFAOYSA-N 0.000 description 1
- RUELTTOHQODFPA-UHFFFAOYSA-N toluene 2,6-diisocyanate Chemical compound CC1=C(N=C=O)C=CC=C1N=C=O RUELTTOHQODFPA-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- 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
- B32B7/00—Layered products characterised by the relation between layers; Layered products characterised by the relative orientation of features between layers, or by the relative values of a measurable parameter between layers, i.e. products comprising layers having different physical, chemical or physicochemical properties; Layered products characterised by the interconnection of layers
- B32B7/04—Interconnection of layers
- B32B7/12—Interconnection of layers using interposed adhesives or interposed materials with bonding properties
-
- 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
- B32B27/00—Layered products comprising a layer of synthetic resin
- B32B27/04—Layered products comprising a layer of synthetic resin as impregnant, bonding, or embedding substance
-
- 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
- B32B27/00—Layered products comprising a layer of synthetic resin
- B32B27/06—Layered products comprising a layer of synthetic resin as the main or only constituent of a layer, which is next to another layer of the same or of a different material
- B32B27/08—Layered products comprising a layer of synthetic resin as the main or only constituent of a layer, which is next to another layer of the same or of a different material of synthetic resin
-
- 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
- C08G18/28—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the compounds used containing active hydrogen
- C08G18/30—Low-molecular-weight compounds
- C08G18/32—Polyhydroxy compounds; Polyamines; Hydroxyamines
- C08G18/3225—Polyamines
- C08G18/3237—Polyamines aromatic
- C08G18/324—Polyamines aromatic containing only one aromatic ring
-
- 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
- C08G18/28—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the compounds used containing active hydrogen
- C08G18/65—Low-molecular-weight compounds having active hydrogen with high-molecular-weight compounds having active hydrogen
- C08G18/66—Compounds of groups C08G18/42, C08G18/48, or C08G18/52
- C08G18/6603—Compounds of groups C08G18/42, C08G18/48, or C08G18/52 with compounds of group C08G18/32 or polyamines of C08G18/38
- C08G18/6614—Compounds of groups C08G18/42, C08G18/48, or C08G18/52 with compounds of group C08G18/32 or polyamines of C08G18/38 with compounds of group C08G18/3225 or C08G18/3271 and/or polyamines of C08G18/38
- C08G18/6618—Compounds of groups C08G18/42, C08G18/48, or C08G18/52 with compounds of group C08G18/32 or polyamines of C08G18/38 with compounds of group C08G18/3225 or C08G18/3271 and/or polyamines of C08G18/38 with compounds of group C08G18/3225 or polyamines of C08G18/38
-
- 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
- C09J175/12—Polyurethanes from compounds containing nitrogen and active hydrogen, the nitrogen atom not being part of an isocyanate group
-
- 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
- B32B2262/00—Composition or structural features of fibres which form a fibrous or filamentary layer or are present as additives
- B32B2262/10—Inorganic fibres
- B32B2262/101—Glass fibres
-
- 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
- Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
- Y10T—TECHNICAL SUBJECTS COVERED BY FORMER US CLASSIFICATION
- Y10T428/00—Stock material or miscellaneous articles
- Y10T428/31504—Composite [nonstructural laminate]
- Y10T428/31551—Of polyamidoester [polyurethane, polyisocyanate, polycarbamate, etc.]
- Y10T428/31598—Next to silicon-containing [silicone, cement, etc.] layer
- Y10T428/31601—Quartz or glass
-
- 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
- Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
- Y10T—TECHNICAL SUBJECTS COVERED BY FORMER US CLASSIFICATION
- Y10T428/00—Stock material or miscellaneous articles
- Y10T428/31504—Composite [nonstructural laminate]
- Y10T428/31551—Of polyamidoester [polyurethane, polyisocyanate, polycarbamate, etc.]
- Y10T428/31616—Next to polyester [e.g., alkyd]
-
- 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
- Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
- Y10T—TECHNICAL SUBJECTS COVERED BY FORMER US CLASSIFICATION
- Y10T428/00—Stock material or miscellaneous articles
- Y10T428/31504—Composite [nonstructural laminate]
- Y10T428/31786—Of polyester [e.g., alkyd, etc.]
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)
- Laminated Bodies (AREA)
- Polyurethanes Or Polyureas (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US06/273,133 US4336298A (en) | 1981-06-12 | 1981-06-12 | Adhesive composition and composite made therewith |
| US273,133 | 1981-06-12 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA1192341A true CA1192341A (en) | 1985-08-20 |
Family
ID=23042675
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA000403884A Expired CA1192341A (en) | 1981-06-12 | 1982-05-27 | Adhesive composition and composite made therewith |
Country Status (5)
| Country | Link |
|---|---|
| US (1) | US4336298A (show.php) |
| EP (1) | EP0068209B1 (show.php) |
| JP (1) | JPS57207667A (show.php) |
| CA (1) | CA1192341A (show.php) |
| DE (1) | DE3262634D1 (show.php) |
Families Citing this family (32)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4853267A (en) * | 1984-02-09 | 1989-08-01 | Minnesota Mining And Manufacturing Company | Easy open closure system |
| JPS61228075A (ja) * | 1985-04-02 | 1986-10-11 | Meisei Kogyo Kk | 接着剤組成物 |
| US4954199A (en) * | 1986-05-30 | 1990-09-04 | Mobay Corporation | Two component polyurethane adhesive |
| CA1279249C (en) * | 1986-05-30 | 1991-01-22 | Randall C. Rains | Two component polyurethane adhesive |
| JPS63150364A (ja) * | 1986-12-12 | 1988-06-23 | Honda Motor Co Ltd | 合成樹脂製構造用外板 |
| DE3727847A1 (de) | 1987-08-20 | 1989-03-02 | Fuller H B Co | Schmelzklebstoff und verfahren zu seiner herstellung und verarbeitung |
| US4876308A (en) * | 1988-02-18 | 1989-10-24 | Gencorp Inc. | Polyurethane adhesive for a surface treatment-free fiber reinforced plastic |
| US5231147A (en) * | 1989-04-10 | 1993-07-27 | Rheox, Inc. | Thermosetting polyurethane structural adhesive compositions and processes for producing the same |
| DE3919697A1 (de) * | 1989-06-16 | 1990-12-20 | Bayer Ag | Einkomponenten-reaktivklebstoffe auf polyurethanbasis |
| US5164473A (en) * | 1990-01-16 | 1992-11-17 | Miles Inc. | Two-component polyurethane adhesive |
| US5204439A (en) * | 1990-01-16 | 1993-04-20 | Miles Inc. | Two-component polyurethane adhesive |
| US4994540A (en) * | 1990-01-16 | 1991-02-19 | Mobay Corporation | Sag resistant, unfilled, low viscosity urethane structural adhesive |
| JPH03283354A (ja) * | 1990-03-30 | 1991-12-13 | Shin Kobe Electric Mach Co Ltd | 密閉形鉛電池 |
| DE4033221A1 (de) * | 1990-10-19 | 1992-04-23 | Bayer Ag | Zweikomponenten-polyurethanklebstoffe |
| US5308657A (en) * | 1991-09-11 | 1994-05-03 | Miles Inc. | Protection of furniture edging |
| DE4138246A1 (de) * | 1991-11-21 | 1993-05-27 | Bayer Ag | Zweikomponenten-polyurethan-reaktivmassen |
| US5175228A (en) * | 1991-12-09 | 1992-12-29 | Gencorp Inc. | Two-component primerless urethane-isocyanurate adhesive compositions having high temperature resistance |
| US5340901A (en) * | 1991-12-09 | 1994-08-23 | Gencorp Inc. | Two-component, primerless, organic phosphorus containing polyurethane adhesive |
| US6746626B2 (en) * | 1994-06-20 | 2004-06-08 | Sgl Technic Inc. | Graphite polymers and methods of use |
| US6001248A (en) * | 1994-08-25 | 1999-12-14 | The University Of Iowa Research Foundation | Gradient interface magnetic composites and systems therefor |
| US5606003A (en) * | 1994-09-01 | 1997-02-25 | Gencorp Inc. | Primerless urethane adhesive compositions |
| US5668211A (en) * | 1996-12-18 | 1997-09-16 | Bayer Corporation | Two-component polyurethane adhesive |
| US5719252A (en) * | 1996-12-18 | 1998-02-17 | Bayer Corporation | Unfilled two-component polyurethane adhesive |
| US6423810B1 (en) | 2001-02-05 | 2002-07-23 | Lord Corporation | High strength, long-open time structural polyurethane adhesive and method of use thereof |
| US6866743B2 (en) | 2001-04-12 | 2005-03-15 | Air Products And Chemicals, Inc. | Controlled structure polyurethane prepolymers for polyurethane structural adhesives |
| KR101498308B1 (ko) * | 2007-03-19 | 2015-03-03 | 바스프 에스이 | 폴리우레탄 샌드위치 부품을 제조하기 위한 폴리우레탄 시스템 |
| EP2501762B1 (de) * | 2009-11-16 | 2016-07-13 | Saint-Gobain Isover | Verwendung eines kleb- und dichtstoffsystems zum verkleben von dampfbremsfolien |
| DE102009046739B4 (de) * | 2009-11-16 | 2020-03-05 | Saint-Gobain Isover G+H Ag | Zweikomponentiges Kleb- und Dichtstoffsystem |
| CN103189410B (zh) * | 2010-11-03 | 2016-07-06 | 汉高股份有限及两合公司 | 具有触变效应的双组分聚氨酯粘合剂 |
| EP2468789A1 (de) | 2010-12-24 | 2012-06-27 | Sika Technology AG | Klebstoff für Rotorblätter für Windkraftanlagen |
| CN110114380B (zh) | 2016-12-28 | 2022-04-26 | 汉高股份有限及两合公司 | 双组分聚氨酯粘合剂 |
| JP7004090B2 (ja) * | 2018-12-21 | 2022-01-21 | Dic株式会社 | 接着剤、積層フィルム、及び積層フィルムの製造方法 |
Family Cites Families (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3248371A (en) * | 1961-03-10 | 1966-04-26 | Wyandotte Chemicals Corp | Cross-linking blocked two-step prepolymer polyurethane coating compositions |
| US3812003A (en) * | 1970-02-11 | 1974-05-21 | Goodyear Tire & Rubber | Polyurethane composition and laminates made therewith |
| JPS53141345A (en) * | 1977-05-17 | 1978-12-09 | Sumitomo Bakelite Co Ltd | Adhesive composition |
| US4247676A (en) * | 1979-08-13 | 1981-01-27 | The Goodyear Tire & Rubber Company | Storable flowable polyurethane adhesive composition |
| US4296212A (en) * | 1980-08-27 | 1981-10-20 | The Upjohn Company | Elastomeric polyurethane-polyurea polymer prepared from an organic polyisocyanate a polyol and an aromatic diamine having at least one of the ortho positions to each amine lower alkyl |
-
1981
- 1981-06-12 US US06/273,133 patent/US4336298A/en not_active Expired - Fee Related
-
1982
- 1982-05-27 CA CA000403884A patent/CA1192341A/en not_active Expired
- 1982-05-27 JP JP57088965A patent/JPS57207667A/ja active Granted
- 1982-06-09 EP EP82105060A patent/EP0068209B1/en not_active Expired
- 1982-06-09 DE DE8282105060T patent/DE3262634D1/de not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| EP0068209B1 (en) | 1985-03-20 |
| EP0068209A1 (en) | 1983-01-05 |
| JPH0252669B2 (show.php) | 1990-11-14 |
| JPS57207667A (en) | 1982-12-20 |
| US4336298A (en) | 1982-06-22 |
| DE3262634D1 (en) | 1985-04-25 |
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