WO2000014137A1 - Impact resistant polyurethane and method of manufacture thereof - Google Patents
Impact resistant polyurethane and method of manufacture thereof Download PDFInfo
- Publication number
- WO2000014137A1 WO2000014137A1 PCT/US1998/021250 US9821250W WO0014137A1 WO 2000014137 A1 WO2000014137 A1 WO 2000014137A1 US 9821250 W US9821250 W US 9821250W WO 0014137 A1 WO0014137 A1 WO 0014137A1
- Authority
- WO
- WIPO (PCT)
- Prior art keywords
- polyurethane material
- group
- polyurethane
- mixtures
- prepolymer
- Prior art date
Links
- 0 C[C@@](CC(CC1(*=I)N)*(C(CC2*)=O)C2=O)(*1*=C)N=C Chemical compound C[C@@](CC(CC1(*=I)N)*(C(CC2*)=O)C2=O)(*1*=C)N=C 0.000 description 1
Classifications
-
- 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
- C08G18/02—Polymeric products of isocyanates or isothiocyanates of isocyanates or isothiocyanates only
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G18/00—Polymeric products of isocyanates or isothiocyanates
- C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
- C08G18/70—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the isocyanates or isothiocyanates used
- C08G18/72—Polyisocyanates or polyisothiocyanates
- C08G18/74—Polyisocyanates or polyisothiocyanates cyclic
- C08G18/75—Polyisocyanates or polyisothiocyanates cyclic cycloaliphatic
- C08G18/758—Polyisocyanates or polyisothiocyanates cyclic cycloaliphatic containing two or more cycloaliphatic rings
-
- 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
-
- 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
- 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
- C08G18/40—High-molecular-weight compounds
- C08G18/4009—Two or more macromolecular compounds not provided for in one single group of groups C08G18/42 - C08G18/64
- C08G18/4018—Mixtures of compounds of group C08G18/42 with compounds of group C08G18/48
-
- 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
- C08G18/40—High-molecular-weight compounds
- C08G18/42—Polycondensates having carboxylic or carbonic ester groups in the main chain
- C08G18/4236—Polycondensates having carboxylic or carbonic ester groups in the main chain containing only aliphatic groups
- C08G18/4238—Polycondensates having carboxylic or carbonic ester groups in the main chain containing only aliphatic groups derived from dicarboxylic acids and dialcohols
-
- 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
- C08G18/40—High-molecular-weight compounds
- C08G18/42—Polycondensates having carboxylic or carbonic ester groups in the main chain
- C08G18/4266—Polycondensates having carboxylic or carbonic ester groups in the main chain prepared from hydroxycarboxylic acids and/or lactones
- C08G18/4269—Lactones
- C08G18/4277—Caprolactone and/or substituted caprolactone
-
- 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
- C08G18/40—High-molecular-weight compounds
- C08G18/42—Polycondensates having carboxylic or carbonic ester groups in the main chain
- C08G18/44—Polycarbonates
-
- 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
- C08G18/40—High-molecular-weight compounds
- C08G18/48—Polyethers
- C08G18/4854—Polyethers containing oxyalkylene groups having four carbon atoms in the alkylene group
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G18/00—Polymeric products of isocyanates or isothiocyanates
- C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
- C08G18/70—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the isocyanates or isothiocyanates used
- C08G18/72—Polyisocyanates or polyisothiocyanates
- C08G18/74—Polyisocyanates or polyisothiocyanates cyclic
- C08G18/76—Polyisocyanates or polyisothiocyanates cyclic aromatic
- C08G18/7614—Polyisocyanates or polyisothiocyanates cyclic aromatic containing only one aromatic ring
- C08G18/7628—Polyisocyanates or polyisothiocyanates cyclic aromatic containing only one aromatic ring containing at least one isocyanate or isothiocyanate group linked to the aromatic ring by means of an aliphatic group
- C08G18/7642—Polyisocyanates or polyisothiocyanates cyclic aromatic containing only one aromatic ring containing at least one isocyanate or isothiocyanate group linked to the aromatic ring by means of an aliphatic group containing at least two isocyanate or isothiocyanate groups linked to the aromatic ring by means of an aliphatic group having a primary carbon atom next to the isocyanate or isothiocyanate groups, e.g. xylylene diisocyanate or homologues substituted on the aromatic ring
Definitions
- optically clear polyurethane of this invention can be prepared by first producing a prepolymer by reacting one or more polyester glycols, polycaprolactone glycols, polyether glycols, or polycarbonate glycols having
- the prepolymer is then reacted with an aromatic diamine curing agent such as diethyltoluene diamine in an equivalent ratio of about
- the OH-containing intermediates which can be used to prepare the polyurethanes of this invention include polyester glycols, polycaprolactone glycols, polyether glycols, and polycarbonate glycols having a weight aver ⁇
- age molecular weight of from about 400 to about 2000, preferrably about
- useful OH-containing intermediates may include
- the preferred aromatic diamine curing agents for use in preparing the polyurethanes of the invention are 2, 4-diamino-3, 5-diethyl-toluene, 2,6- diamino-3, 5-diethyl-toluene and mixtures thereof (collectively "diethyltoluenediamine” or "DETDA”), which is sold by Albemarle Corporation under the trade name Ethacure 100.
- DETDA is a liquid at room temperature with a viscosity of 156 cs at 25°C.
- DETDA is isomeric,
- the diisocyanate is first mixed with the OH-
- the prepolymer is then reacted at about 160°F to 180°F with the
- the prepolymer may be added to the prepolymer in an amount of up to 5% by weight based
- the prepolymer is cooled to 220° to 250°F, and the
- the prepolymer is then reacted at about 160°F to 180°F with an
- the polyurethane materials of Examples I-rV all have excellent optical characteristics
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- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Organic Chemistry (AREA)
- Polyurethanes Or Polyureas (AREA)
- Graft Or Block Polymers (AREA)
- Organic Insulating Materials (AREA)
- Compositions Of Macromolecular Compounds (AREA)
Abstract
Description
Claims
Priority Applications (11)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
IL14170998A IL141709A0 (en) | 1998-09-02 | 1998-10-07 | Impact resistant polyurethane and method of manufacture thereof |
CA002342851A CA2342851C (en) | 1998-09-02 | 1998-10-07 | Impact resistant polyurethane and method of manufacture thereof |
MXPA01002291A MXPA01002291A (en) | 1998-09-02 | 1998-10-07 | Impact resistant polyurethane and method of manufacture thereof. |
AT98948609T ATE274004T1 (en) | 1998-09-02 | 1998-10-07 | IMPACT POLYURETHANE AND METHOD FOR PRODUCTION |
DE69825796T DE69825796T2 (en) | 1998-09-02 | 1998-10-07 | IMPACT POLYURETHANE AND METHOD OF MANUFACTURE |
JP2000568891A JP4898001B2 (en) | 1998-09-02 | 1998-10-07 | Impact resistant polyurethane and process for producing the same |
EP98948609A EP1137684B1 (en) | 1998-09-02 | 1998-10-07 | Impact resistant polyurethane and method of manufacture thereof |
AU95144/98A AU762846B2 (en) | 1998-09-02 | 1998-10-07 | Impact resistant polyurethane and method of manufacture thereof |
IL141709A IL141709A (en) | 1998-09-02 | 2001-02-28 | Impact resistant polyurethane and method of manufacture thereof |
NO20011064A NO328118B1 (en) | 1998-09-02 | 2001-03-01 | Impact resistant polyurethane materials and oil lens produced therefrom |
HK02102529.4A HK1042311B (en) | 1998-09-02 | 2002-04-04 | Impact resistant polyurethane and method of manufacture thereof |
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US09/145,658 US6127505A (en) | 1995-02-02 | 1998-09-02 | Impact resistant polyurethane and method of manufacture thereof |
US09/145,658 | 1998-09-02 |
Publications (1)
Publication Number | Publication Date |
---|---|
WO2000014137A1 true WO2000014137A1 (en) | 2000-03-16 |
Family
ID=22514025
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
PCT/US1998/021250 WO2000014137A1 (en) | 1998-09-02 | 1998-10-07 | Impact resistant polyurethane and method of manufacture thereof |
Country Status (18)
Country | Link |
---|---|
US (1) | US6127505A (en) |
EP (1) | EP1137684B1 (en) |
JP (1) | JP4898001B2 (en) |
KR (1) | KR100526050B1 (en) |
CN (2) | CN1654499B (en) |
AT (1) | ATE274004T1 (en) |
AU (1) | AU762846B2 (en) |
CA (1) | CA2342851C (en) |
DE (1) | DE69825796T2 (en) |
ES (1) | ES2227879T3 (en) |
HK (1) | HK1042311B (en) |
ID (1) | ID29092A (en) |
IL (2) | IL141709A0 (en) |
MX (1) | MXPA01002291A (en) |
MY (1) | MY118596A (en) |
NO (1) | NO328118B1 (en) |
TW (1) | TW546315B (en) |
WO (1) | WO2000014137A1 (en) |
Cited By (31)
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EP1182219A1 (en) * | 2000-08-23 | 2002-02-27 | Basf Aktiengesellschaft | Process for the preparation of compact transparent shoe parts |
WO2003044071A1 (en) * | 2001-11-16 | 2003-05-30 | Ppg Industries Ohio, Inc. | Impact resistant polyureaurethane and method of preparation |
WO2003080693A2 (en) * | 2001-11-16 | 2003-10-02 | Ppg Industries Ohio, Inc. | Impact resistant polyureaurethane and polyureaurethane prepolymer having low nco/oh ratio |
WO2004060951A1 (en) * | 2002-12-20 | 2004-07-22 | Ppg Industries Ohio, Inc. | High impact poly(urethane urea) polysulfides |
WO2007096425A2 (en) * | 2006-02-24 | 2007-08-30 | Essilor International (Compagnie Generale D'optique) | Process for manufacturing a polarized poly(thio)urethane optical lens |
EP1950235A1 (en) * | 2005-10-27 | 2008-07-30 | Hitachi Chemical Company, Ltd. | Resin composition and optical member formed from the same |
JP2009052053A (en) * | 2001-10-12 | 2009-03-12 | Bayer Corp | Light-stable polyurethane-urea elastomer and its production process |
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US8207286B2 (en) | 2004-09-01 | 2012-06-26 | Ppg Industries Ohio, Inc | Methods for preparing polyurethanes |
US8349986B2 (en) | 2004-09-01 | 2013-01-08 | Ppg Industries Ohio, Inc. | Poly(ureaurethane)s, articles and coatings prepared therefrom and methods of making the same |
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US8604153B2 (en) | 2004-09-01 | 2013-12-10 | Ppg Industries Ohio, Inc. | Poly(ureaurethane)s, articles and coatings prepared therefrom and methods of making the same |
US8653220B2 (en) | 2004-09-01 | 2014-02-18 | Ppg Industries Ohio, Inc. | Poly(ureaurethane)s, articles and coatings prepared therefrom and methods of making the same |
US8734951B2 (en) | 2004-09-01 | 2014-05-27 | Ppg Industries Ohio, Inc. | Polyurethanes, articles and coatings prepared therefrom and methods of making the same |
US8835592B2 (en) | 2004-09-01 | 2014-09-16 | Ppg Industries Ohio, Inc. | Polyurethanes, articles and coatings prepared therefrom and methods of making the same |
US8859680B2 (en) | 2004-09-01 | 2014-10-14 | Ppg Industries Ohio, Inc | Poly(ureaurethane)s, articles and coatings prepared therefrom and methods of making the same |
US8889815B2 (en) | 2004-09-01 | 2014-11-18 | Ppg Industries Ohio, Inc. | Reinforced polyurethanes and poly(ureaurethane)s, methods of making the same and articles prepared therefrom |
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ATE274004T1 (en) | 2004-09-15 |
CN1654499B (en) | 2012-05-30 |
CN1188442C (en) | 2005-02-09 |
HK1042311A1 (en) | 2002-08-09 |
MXPA01002291A (en) | 2002-05-08 |
US6127505A (en) | 2000-10-03 |
IL141709A (en) | 2010-05-17 |
ID29092A (en) | 2001-07-26 |
NO20011064D0 (en) | 2001-03-01 |
KR20010074892A (en) | 2001-08-09 |
NO20011064L (en) | 2001-04-23 |
JP2002524591A (en) | 2002-08-06 |
DE69825796T2 (en) | 2005-01-27 |
CN1314922A (en) | 2001-09-26 |
EP1137684B1 (en) | 2004-08-18 |
MY118596A (en) | 2004-12-31 |
KR100526050B1 (en) | 2005-11-08 |
ES2227879T3 (en) | 2005-04-01 |
CA2342851A1 (en) | 2000-03-16 |
JP4898001B2 (en) | 2012-03-14 |
CA2342851C (en) | 2009-12-15 |
AU9514498A (en) | 2000-03-27 |
EP1137684A1 (en) | 2001-10-04 |
HK1042311B (en) | 2005-02-04 |
AU762846B2 (en) | 2003-07-10 |
TW546315B (en) | 2003-08-11 |
DE69825796D1 (en) | 2004-09-23 |
EP1137684A4 (en) | 2002-03-20 |
NO328118B1 (en) | 2009-12-14 |
IL141709A0 (en) | 2002-03-10 |
CN1654499A (en) | 2005-08-17 |
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