CN1240738C - 用于聚氨酯结构粘合剂的控制结构聚氨酯预聚物 - Google Patents
用于聚氨酯结构粘合剂的控制结构聚氨酯预聚物 Download PDFInfo
- Publication number
- CN1240738C CN1240738C CNB02105522XA CN02105522A CN1240738C CN 1240738 C CN1240738 C CN 1240738C CN B02105522X A CNB02105522X A CN B02105522XA CN 02105522 A CN02105522 A CN 02105522A CN 1240738 C CN1240738 C CN 1240738C
- Authority
- CN
- China
- Prior art keywords
- prepolymer
- polyurethane
- reaction product
- adhesive
- diisocyanate
- 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 - Lifetime
Links
- 239000000853 adhesive Substances 0.000 title claims abstract description 42
- 230000001070 adhesive effect Effects 0.000 title claims abstract description 42
- 229920002635 polyurethane Polymers 0.000 title claims abstract description 29
- 239000004814 polyurethane Substances 0.000 title claims abstract description 29
- 229920001730 Moisture cure polyurethane Polymers 0.000 title claims description 20
- 239000000203 mixture Substances 0.000 claims abstract description 36
- 239000007795 chemical reaction product Substances 0.000 claims abstract description 21
- 239000000178 monomer Substances 0.000 claims abstract description 16
- IQPQWNKOIGAROB-UHFFFAOYSA-N isocyanate group Chemical group [N-]=C=O IQPQWNKOIGAROB-UHFFFAOYSA-N 0.000 claims abstract description 3
- 239000000463 material Substances 0.000 claims description 31
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 claims description 26
- 239000003795 chemical substances by application Substances 0.000 claims description 26
- 239000005056 polyisocyanate Substances 0.000 claims description 19
- 229920001228 polyisocyanate Polymers 0.000 claims description 19
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 18
- 238000010276 construction Methods 0.000 claims description 15
- DVKJHBMWWAPEIU-UHFFFAOYSA-N toluene 2,4-diisocyanate Chemical compound CC1=CC=C(N=C=O)C=C1N=C=O DVKJHBMWWAPEIU-UHFFFAOYSA-N 0.000 claims description 14
- 239000011230 binding agent Substances 0.000 claims description 11
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 claims description 10
- 229920000570 polyether Polymers 0.000 claims description 10
- 238000000034 method Methods 0.000 claims description 9
- 239000004721 Polyphenylene oxide Substances 0.000 claims description 6
- VNWKTOKETHGBQD-UHFFFAOYSA-N methane Chemical compound C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 claims description 6
- 229920005906 polyester polyol Polymers 0.000 claims description 5
- 239000000047 product Substances 0.000 claims description 5
- NIMLQBUJDJZYEJ-UHFFFAOYSA-N isophorone diisocyanate Chemical compound CC1(C)CC(N=C=O)CC(C)(CN=C=O)C1 NIMLQBUJDJZYEJ-UHFFFAOYSA-N 0.000 claims description 4
- 239000005057 Hexamethylene diisocyanate Substances 0.000 claims description 3
- 239000005058 Isophorone diisocyanate Substances 0.000 claims description 3
- 230000015572 biosynthetic process Effects 0.000 claims description 3
- RRAMGCGOFNQTLD-UHFFFAOYSA-N hexamethylene diisocyanate Chemical compound O=C=NCCCCCCN=C=O RRAMGCGOFNQTLD-UHFFFAOYSA-N 0.000 claims description 3
- 125000000843 phenylene group Chemical group C1(=C(C=CC=C1)*)* 0.000 claims description 3
- 150000005846 sugar alcohols Polymers 0.000 claims description 2
- 239000012948 isocyanate Substances 0.000 abstract description 10
- 150000002513 isocyanates Chemical class 0.000 abstract description 10
- -1 polytrimethylene Polymers 0.000 description 12
- 239000002131 composite material Substances 0.000 description 10
- 150000002148 esters Chemical class 0.000 description 9
- 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 8
- 239000010960 cold rolled steel Substances 0.000 description 8
- 238000002360 preparation method Methods 0.000 description 8
- 229920000728 polyester Polymers 0.000 description 7
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 5
- 239000002253 acid Substances 0.000 description 5
- 238000006243 chemical reaction Methods 0.000 description 5
- 150000004985 diamines Chemical group 0.000 description 5
- 238000010008 shearing Methods 0.000 description 5
- 239000000654 additive Substances 0.000 description 4
- 229910052782 aluminium Inorganic materials 0.000 description 4
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 4
- 239000004411 aluminium Substances 0.000 description 4
- 230000008901 benefit Effects 0.000 description 4
- 238000009472 formulation Methods 0.000 description 4
- 229920005862 polyol Polymers 0.000 description 4
- 150000003077 polyols Chemical class 0.000 description 4
- 239000011701 zinc Substances 0.000 description 4
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 3
- 230000000996 additive effect Effects 0.000 description 3
- 125000004356 hydroxy functional group Chemical group O* 0.000 description 3
- 239000003973 paint Substances 0.000 description 3
- 239000000843 powder Substances 0.000 description 3
- 230000037452 priming Effects 0.000 description 3
- 238000007665 sagging Methods 0.000 description 3
- 238000012360 testing method Methods 0.000 description 3
- PUPZLCDOIYMWBV-UHFFFAOYSA-N (+/-)-1,3-Butanediol Chemical compound CC(O)CCO PUPZLCDOIYMWBV-UHFFFAOYSA-N 0.000 description 2
- 239000004831 Hot glue Substances 0.000 description 2
- NSOXQYCFHDMMGV-UHFFFAOYSA-N Tetrakis(2-hydroxypropyl)ethylenediamine Chemical compound CC(O)CN(CC(C)O)CCN(CC(C)O)CC(C)O NSOXQYCFHDMMGV-UHFFFAOYSA-N 0.000 description 2
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 2
- 239000012141 concentrate Substances 0.000 description 2
- 238000013461 design Methods 0.000 description 2
- 238000009826 distribution Methods 0.000 description 2
- 238000005516 engineering process Methods 0.000 description 2
- 239000011521 glass Substances 0.000 description 2
- 239000003365 glass fiber Substances 0.000 description 2
- 238000009998 heat setting Methods 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- 239000011325 microbead Substances 0.000 description 2
- 238000002156 mixing Methods 0.000 description 2
- 229920001451 polypropylene glycol Polymers 0.000 description 2
- 238000012545 processing Methods 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- 230000008719 thickening Effects 0.000 description 2
- 229910052725 zinc Inorganic materials 0.000 description 2
- 229920001634 Copolyester Polymers 0.000 description 1
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 1
- 239000002202 Polyethylene glycol Substances 0.000 description 1
- 239000004743 Polypropylene Substances 0.000 description 1
- GOOHAUXETOMSMM-UHFFFAOYSA-N Propylene oxide Chemical compound CC1CO1 GOOHAUXETOMSMM-UHFFFAOYSA-N 0.000 description 1
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
- ATJFFYVFTNAWJD-UHFFFAOYSA-N Tin Chemical compound [Sn] ATJFFYVFTNAWJD-UHFFFAOYSA-N 0.000 description 1
- XSTXAVWGXDQKEL-UHFFFAOYSA-N Trichloroethylene Chemical compound ClC=C(Cl)Cl XSTXAVWGXDQKEL-UHFFFAOYSA-N 0.000 description 1
- QCWXUUIWCKQGHC-UHFFFAOYSA-N Zirconium Chemical compound [Zr] QCWXUUIWCKQGHC-UHFFFAOYSA-N 0.000 description 1
- DHKHKXVYLBGOIT-UHFFFAOYSA-N acetaldehyde Diethyl Acetal Natural products CCOC(C)OCC DHKHKXVYLBGOIT-UHFFFAOYSA-N 0.000 description 1
- 229920000122 acrylonitrile butadiene styrene Polymers 0.000 description 1
- 239000004676 acrylonitrile butadiene styrene Substances 0.000 description 1
- WNLRTRBMVRJNCN-UHFFFAOYSA-L adipate(2-) Chemical compound [O-]C(=O)CCCCC([O-])=O WNLRTRBMVRJNCN-UHFFFAOYSA-L 0.000 description 1
- 230000004523 agglutinating effect Effects 0.000 description 1
- 230000032683 aging Effects 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 125000001931 aliphatic group Chemical group 0.000 description 1
- 125000003368 amide group Chemical group 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 239000002518 antifoaming agent Substances 0.000 description 1
- 150000004982 aromatic amines Chemical class 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- 229910052797 bismuth Inorganic materials 0.000 description 1
- JCXGWMGPZLAOME-UHFFFAOYSA-N bismuth atom Chemical compound [Bi] JCXGWMGPZLAOME-UHFFFAOYSA-N 0.000 description 1
- 238000004364 calculation method Methods 0.000 description 1
- 230000008859 change Effects 0.000 description 1
- 239000011248 coating agent Substances 0.000 description 1
- 238000000576 coating method Methods 0.000 description 1
- 238000007334 copolymerization reaction Methods 0.000 description 1
- 150000004292 cyclic ethers Chemical class 0.000 description 1
- 125000005442 diisocyanate group Chemical group 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 229910021485 fumed silica Inorganic materials 0.000 description 1
- 125000000524 functional group Chemical group 0.000 description 1
- 229920000578 graft copolymer Polymers 0.000 description 1
- 230000036541 health Effects 0.000 description 1
- 150000002466 imines Chemical class 0.000 description 1
- 229910052500 inorganic mineral Inorganic materials 0.000 description 1
- 238000011835 investigation Methods 0.000 description 1
- 239000012939 laminating adhesive Substances 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 239000000155 melt Substances 0.000 description 1
- 239000003863 metallic catalyst Substances 0.000 description 1
- 239000011707 mineral Substances 0.000 description 1
- 238000005457 optimization Methods 0.000 description 1
- 125000002524 organometallic group Chemical group 0.000 description 1
- AHHWIHXENZJRFG-UHFFFAOYSA-N oxetane Chemical compound C1COC1 AHHWIHXENZJRFG-UHFFFAOYSA-N 0.000 description 1
- ZHZCYWWNFQUZOR-UHFFFAOYSA-N pent-4-en-2-ol Chemical group CC(O)CC=C ZHZCYWWNFQUZOR-UHFFFAOYSA-N 0.000 description 1
- 229920001281 polyalkylene Polymers 0.000 description 1
- 229920000515 polycarbonate Polymers 0.000 description 1
- 239000004417 polycarbonate Substances 0.000 description 1
- 229920001223 polyethylene glycol Polymers 0.000 description 1
- 229920000139 polyethylene terephthalate Polymers 0.000 description 1
- 239000005020 polyethylene terephthalate Substances 0.000 description 1
- 239000004848 polyfunctional curative Substances 0.000 description 1
- 229920001470 polyketone Polymers 0.000 description 1
- 229920000642 polymer Polymers 0.000 description 1
- 229920001155 polypropylene Polymers 0.000 description 1
- 229920000915 polyvinyl chloride Polymers 0.000 description 1
- 239000004800 polyvinyl chloride Substances 0.000 description 1
- 150000003141 primary amines Chemical class 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 230000004044 response Effects 0.000 description 1
- 238000007789 sealing Methods 0.000 description 1
- 125000003198 secondary alcohol group Chemical group 0.000 description 1
- 150000003335 secondary amines Chemical class 0.000 description 1
- 239000011343 solid material Substances 0.000 description 1
- 239000000758 substrate Substances 0.000 description 1
- 238000004381 surface treatment Methods 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- 235000012222 talc Nutrition 0.000 description 1
- 125000001650 tertiary alcohol group Chemical group 0.000 description 1
- 239000012970 tertiary amine catalyst Substances 0.000 description 1
- 229920002397 thermoplastic olefin Polymers 0.000 description 1
- 229910052718 tin Inorganic materials 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
- 229920002554 vinyl polymer Polymers 0.000 description 1
- 229910052726 zirconium Inorganic materials 0.000 description 1
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
- 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
- C09J175/08—Polyurethanes from polyethers
-
- 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
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
预聚物 | 异氰酸酯 | 多元醇 | %NCO | 残余二异氰酸酯(wt%) | %低聚物 |
1 | MDI | PPG-型 | 6.6 | 0.4 | 8 |
2 | MDI | PPG-型 | 6.6 | >5 | >50 |
3 | MDI | PPG-型 | 6.7 | 0.6 | 4 |
4 | MDI | PPG-型 | 6.5 | >5 | >50 |
5 | TDI | PPG-型 | 7.47 | <0.1 | <1 |
6 | TDI | PPG-型 | 7.80 | 2.2 | 25 |
预聚物 | 基材 | 固化 | 1天后的剪切强度(psi) | 7天后的剪切强度(psi) |
5 | SMC | RT | 614(92) | 701(79) |
6 | SMC | RT | 486(69) | 526(72) |
5 | SMC | 热* | 656(92) | 643(32) |
6 | SMC | 热* | 475(25) | 425(17) |
预聚物 | 固化 | 1天后的剪切强度(psi) | 7天后的剪切强度(psi) | %固化(1d/7d) |
1 | RT | 1324 | 1617 | 82 |
2 | RT | 874 | 1684 | 52 |
3 | RT | 1240 | 1452 | 85 |
4 | RT | 981 | 1367 | 72 |
Claims (10)
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US09/833,453 US6866743B2 (en) | 2001-04-12 | 2001-04-12 | Controlled structure polyurethane prepolymers for polyurethane structural adhesives |
US09/833453 | 2001-04-12 |
Publications (2)
Publication Number | Publication Date |
---|---|
CN1380345A CN1380345A (zh) | 2002-11-20 |
CN1240738C true CN1240738C (zh) | 2006-02-08 |
Family
ID=25264454
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
CNB02105522XA Expired - Lifetime CN1240738C (zh) | 2001-04-12 | 2002-04-12 | 用于聚氨酯结构粘合剂的控制结构聚氨酯预聚物 |
Country Status (7)
Country | Link |
---|---|
US (1) | US6866743B2 (zh) |
EP (1) | EP1253159B1 (zh) |
JP (1) | JP3777479B2 (zh) |
KR (1) | KR100453600B1 (zh) |
CN (1) | CN1240738C (zh) |
AT (1) | ATE332323T1 (zh) |
DE (1) | DE60212894T2 (zh) |
Families Citing this family (27)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US6884904B2 (en) * | 2001-04-12 | 2005-04-26 | Air Products And Chemicals, Inc. | MDI-based polyurethane prepolymer with low monomeric MDI content |
DE50309990D1 (de) * | 2002-02-22 | 2008-07-31 | Jowat Ag | Polyurethan-Zusammensetzungen mit geringem Anteil an Diisocyanatmonomer(en) |
DE10225982B4 (de) * | 2002-06-11 | 2012-04-19 | Jowat Ag | Polyurethan-Zusammensetzungen mit geringem Anteil von Diisocyanatmonomeren |
US20030203771A1 (en) * | 2002-04-26 | 2003-10-30 | Ronald Rosenberg | Polyurethane elastomers from HDI prepolymers with reduced content of free HDI monomers |
DE10351530A1 (de) * | 2003-11-03 | 2005-06-16 | Basf Ag | Verfahren zur Herstellung von Isocyanatgruppen enthaltenden Prepolymeren |
US20050154172A1 (en) * | 2004-01-08 | 2005-07-14 | Conner Mark D. | Low residual monomer IPDI-PPG prepolymer |
US7829637B2 (en) * | 2004-02-17 | 2010-11-09 | Continental Structural Plastics | Polymeric thickener for molding compounds |
KR100586037B1 (ko) | 2004-07-19 | 2006-06-08 | 오주영 | 친환경적 우레탄 시트 및 그 제조방법 |
US20060079661A1 (en) * | 2004-10-08 | 2006-04-13 | Zhu Huide D | Low volatile isocyanate monomer containing polyurethane prepolymer and adhesive system |
US7361292B2 (en) * | 2004-11-08 | 2008-04-22 | Dow Global Technologies Inc. | High modulus, nonconductive adhesive useful for installing vehicle windows |
EP1690880A1 (de) | 2005-02-11 | 2006-08-16 | Sika Technology AG | Zweikomponentige Polyurethanzusammensetzungen, insbesondere geeignet für den Einsatz als strukturelle Klebstoffe |
EP2042539B1 (en) | 2006-06-20 | 2012-10-24 | DIC Corporation | Hyperbranched polyether polyol and urethan resin composition |
EP2183294B1 (en) * | 2007-07-23 | 2019-01-09 | Dow Global Technologies LLC | Two part polyurethane curable composition having substantially consistent g-modulus across the range of use temperatures |
KR101529865B1 (ko) * | 2007-11-07 | 2015-06-19 | 다우 글로벌 테크놀로지스 엘엘씨 | 고도의 충전제 수준을 갖는 폴리우레탄 접착제 조성물 |
KR101650965B1 (ko) * | 2008-08-22 | 2016-08-24 | 다우 글로벌 테크놀로지스 엘엘씨 | 큰 중량의 부품을 구조물에 접착시키기에 적합한 접착제 조성물 |
DE102008039679A1 (de) | 2008-08-26 | 2010-03-04 | Henkel Ag & Co. Kgaa | Verfahren zum Kaschieren von Folien |
DE102008060885A1 (de) | 2008-12-09 | 2010-06-10 | Henkel Ag & Co. Kgaa | PU-Klebstoffen für sterilisierbare Verbundfolien |
CN101463242B (zh) * | 2009-01-22 | 2012-05-09 | 嘉兴禾欣化学工业有限公司 | Pvc薄膜干式复合用双组份环保型聚氨酯胶粘剂及其制造方法 |
US8551201B2 (en) * | 2009-08-07 | 2013-10-08 | Praxair S.T. Technology, Inc. | Polyurethane composition for CMP pads and method of manufacturing same |
CN103370350B (zh) | 2011-02-17 | 2015-05-27 | 陶氏环球技术有限责任公司 | 含有碳酸钙的含烷氧基硅烷的聚氨酯粘合剂组合物 |
CN103497725B (zh) * | 2013-09-26 | 2014-09-17 | 昆山天洋热熔胶有限公司 | 一种纺织品用湿固化反应型聚氨酯热熔胶的制备方法 |
WO2016014290A1 (en) * | 2014-07-25 | 2016-01-28 | Dow Global Technologies Llc | One-component structural adhesive containing isocyanate-terminated prepolymer |
BR112021000681A2 (pt) * | 2018-08-08 | 2021-04-13 | Sika Technology Ag | Composição de poliuretano com baixo teor de diisocianatos monoméricos |
CN113330048A (zh) * | 2019-04-05 | 2021-08-31 | Sika技术股份公司 | 基于二聚脂肪酸聚酯二元醇的含异氰酸酯基团的聚合物 |
CN114450323A (zh) | 2019-09-12 | 2022-05-06 | 朗盛公司 | 低游离聚氨酯预聚物组合物 |
EP4214256B1 (en) | 2020-09-18 | 2024-09-11 | LANXESS Corporation | Low free polyurethane prepolymer composition for reactive hot melt adhesives |
WO2024064070A1 (en) | 2022-09-22 | 2024-03-28 | Lubrizol Advanced Materials, Inc. | Non-softening thermoplastic polyurethanes |
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ATE174042T1 (de) * | 1994-08-22 | 1998-12-15 | Henkel Kgaa | Polyurethan-zusammensetzungen mit niedrigem gehalt an monomeren diisocyanaten |
JPH08176252A (ja) | 1994-12-26 | 1996-07-09 | Mitsui Toatsu Chem Inc | 改良されたプレポリマー組成物 |
GB9608181D0 (en) * | 1996-04-19 | 1996-06-26 | Baxenden Chem Ltd | Moisture curing hot melt adhesives |
CA2214311A1 (en) * | 1996-09-06 | 1998-03-06 | Air Products And Chemicals, Inc. | Hot melt adhesives comprising low free monomer, low oligomer isocyanate prepolymers |
US5955199A (en) | 1997-09-26 | 1999-09-21 | Ashland Inc. | Imine-containing curative for two component polyurethane structural adhesives |
ATE258943T1 (de) | 1999-07-02 | 2004-02-15 | Henkel Kgaa | Verwendung von polyurethanzusammensetzungen mit niedrigen monomergehalt als haftklebstoff |
AU1450201A (en) | 1999-11-30 | 2001-06-12 | Crompton Corporation | High performance polyurethane elastomers from mdi prepolymers with reduced content of free mdi monomer |
US6884904B2 (en) | 2001-04-12 | 2005-04-26 | Air Products And Chemicals, Inc. | MDI-based polyurethane prepolymer with low monomeric MDI content |
-
2001
- 2001-04-12 US US09/833,453 patent/US6866743B2/en not_active Expired - Lifetime
-
2002
- 2002-04-11 AT AT02008125T patent/ATE332323T1/de not_active IP Right Cessation
- 2002-04-11 EP EP02008125A patent/EP1253159B1/en not_active Expired - Lifetime
- 2002-04-11 DE DE60212894T patent/DE60212894T2/de not_active Expired - Lifetime
- 2002-04-11 KR KR10-2002-0019713A patent/KR100453600B1/ko active IP Right Grant
- 2002-04-11 JP JP2002109079A patent/JP3777479B2/ja not_active Expired - Fee Related
- 2002-04-12 CN CNB02105522XA patent/CN1240738C/zh not_active Expired - Lifetime
Also Published As
Publication number | Publication date |
---|---|
JP2002327164A (ja) | 2002-11-15 |
JP3777479B2 (ja) | 2006-05-24 |
EP1253159A1 (en) | 2002-10-30 |
US20030024639A1 (en) | 2003-02-06 |
EP1253159B1 (en) | 2006-07-05 |
US6866743B2 (en) | 2005-03-15 |
KR100453600B1 (ko) | 2004-10-20 |
DE60212894D1 (de) | 2006-08-17 |
ATE332323T1 (de) | 2006-07-15 |
KR20020079582A (ko) | 2002-10-19 |
DE60212894T2 (de) | 2007-06-28 |
CN1380345A (zh) | 2002-11-20 |
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