CA2382031A1 - Method for producing prepolymers containing isocyanate end groups, incorporating a small proportion of base isocyanates - Google Patents
Method for producing prepolymers containing isocyanate end groups, incorporating a small proportion of base isocyanates Download PDFInfo
- Publication number
- CA2382031A1 CA2382031A1 CA002382031A CA2382031A CA2382031A1 CA 2382031 A1 CA2382031 A1 CA 2382031A1 CA 002382031 A CA002382031 A CA 002382031A CA 2382031 A CA2382031 A CA 2382031A CA 2382031 A1 CA2382031 A1 CA 2382031A1
- Authority
- CA
- Canada
- Prior art keywords
- polyesters
- prepolymers
- content
- polyisocyanates
- contain
- 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.)
- Abandoned
Links
- 239000012948 isocyanate Substances 0.000 title claims abstract description 16
- 150000002513 isocyanates Chemical class 0.000 title claims abstract description 16
- 238000004519 manufacturing process Methods 0.000 title claims abstract description 9
- IQPQWNKOIGAROB-UHFFFAOYSA-N isocyanate group Chemical group [N-]=C=O IQPQWNKOIGAROB-UHFFFAOYSA-N 0.000 title abstract description 3
- 239000005056 polyisocyanate Substances 0.000 claims abstract description 14
- 229920000728 polyester Polymers 0.000 claims description 39
- 238000000034 method Methods 0.000 claims description 13
- 229920001228 polyisocyanate Polymers 0.000 claims description 13
- 238000004821 distillation Methods 0.000 claims description 11
- 229920005862 polyol Polymers 0.000 claims description 10
- 150000003077 polyols Chemical class 0.000 claims description 10
- 239000003795 chemical substances by application Substances 0.000 claims description 8
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 8
- 229920001971 elastomer Polymers 0.000 claims description 6
- 239000000806 elastomer Substances 0.000 claims description 6
- 239000004814 polyurethane Substances 0.000 claims description 4
- 239000011541 reaction mixture Substances 0.000 claims description 4
- 238000009826 distribution Methods 0.000 claims description 2
- 229920005906 polyester polyol Polymers 0.000 abstract description 3
- 239000012458 free base Substances 0.000 abstract 1
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 13
- 239000007858 starting material Substances 0.000 description 7
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
- WNLRTRBMVRJNCN-UHFFFAOYSA-N adipic acid Chemical compound OC(=O)CCCCC(O)=O WNLRTRBMVRJNCN-UHFFFAOYSA-N 0.000 description 6
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 6
- 239000000047 product Substances 0.000 description 4
- 239000002253 acid Substances 0.000 description 3
- 235000011037 adipic acid Nutrition 0.000 description 3
- 239000001361 adipic acid Substances 0.000 description 3
- 238000006243 chemical reaction Methods 0.000 description 3
- 230000015572 biosynthetic process Effects 0.000 description 2
- 239000003431 cross linking reagent Substances 0.000 description 2
- 150000002009 diols Chemical class 0.000 description 2
- 230000032050 esterification Effects 0.000 description 2
- 238000005886 esterification reaction Methods 0.000 description 2
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- 239000000178 monomer Substances 0.000 description 2
- 229920002635 polyurethane Polymers 0.000 description 2
- 150000004072 triols Chemical class 0.000 description 2
- HFVMEOPYDLEHBR-UHFFFAOYSA-N (2-fluorophenyl)-phenylmethanol Chemical compound C=1C=CC=C(F)C=1C(O)C1=CC=CC=C1 HFVMEOPYDLEHBR-UHFFFAOYSA-N 0.000 description 1
- RTBFRGCFXZNCOE-UHFFFAOYSA-N 1-methylsulfonylpiperidin-4-one Chemical compound CS(=O)(=O)N1CCC(=O)CC1 RTBFRGCFXZNCOE-UHFFFAOYSA-N 0.000 description 1
- UPZSGWVELOYWER-UHFFFAOYSA-N 3,5-diamino-4-chlorobenzoic acid Chemical compound NC1=CC(C(O)=O)=CC(N)=C1Cl UPZSGWVELOYWER-UHFFFAOYSA-N 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- 238000005684 Liebig rearrangement reaction Methods 0.000 description 1
- KDYFGRWQOYBRFD-UHFFFAOYSA-N Succinic acid Natural products OC(=O)CCC(O)=O KDYFGRWQOYBRFD-UHFFFAOYSA-N 0.000 description 1
- 238000005299 abrasion Methods 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- 125000001931 aliphatic group Chemical group 0.000 description 1
- JFCQEDHGNNZCLN-UHFFFAOYSA-N anhydrous glutaric acid Natural products OC(=O)CCCC(O)=O JFCQEDHGNNZCLN-UHFFFAOYSA-N 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- CDQSJQSWAWPGKG-UHFFFAOYSA-N butane-1,1-diol Chemical compound CCCC(O)O CDQSJQSWAWPGKG-UHFFFAOYSA-N 0.000 description 1
- 125000004432 carbon atom Chemical group C* 0.000 description 1
- 238000005266 casting Methods 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 230000001413 cellular effect Effects 0.000 description 1
- 239000013065 commercial product Substances 0.000 description 1
- 239000000470 constituent Substances 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- 238000001514 detection method Methods 0.000 description 1
- 150000001991 dicarboxylic acids Chemical class 0.000 description 1
- 239000003995 emulsifying agent Substances 0.000 description 1
- 230000007613 environmental effect Effects 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 230000002349 favourable effect Effects 0.000 description 1
- 238000007701 flash-distillation Methods 0.000 description 1
- YMAWOPBAYDPSLA-UHFFFAOYSA-N glycylglycine Chemical compound [NH3+]CC(=O)NCC([O-])=O YMAWOPBAYDPSLA-UHFFFAOYSA-N 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 125000000623 heterocyclic group Chemical group 0.000 description 1
- ACCCMOQWYVYDOT-UHFFFAOYSA-N hexane-1,1-diol Chemical compound CCCCCC(O)O ACCCMOQWYVYDOT-UHFFFAOYSA-N 0.000 description 1
- -1 isobutyl ester Chemical class 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- SYSQUGFVNFXIIT-UHFFFAOYSA-N n-[4-(1,3-benzoxazol-2-yl)phenyl]-4-nitrobenzenesulfonamide Chemical class C1=CC([N+](=O)[O-])=CC=C1S(=O)(=O)NC1=CC=C(C=2OC3=CC=CC=C3N=2)C=C1 SYSQUGFVNFXIIT-UHFFFAOYSA-N 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 239000004033 plastic Substances 0.000 description 1
- 229920003023 plastic Polymers 0.000 description 1
- 239000004014 plasticizer Substances 0.000 description 1
- ULWHHBHJGPPBCO-UHFFFAOYSA-N propane-1,1-diol Chemical compound CCC(O)O ULWHHBHJGPPBCO-UHFFFAOYSA-N 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 239000010409 thin film Substances 0.000 description 1
- 230000001988 toxicity Effects 0.000 description 1
- 231100000419 toxicity Toxicity 0.000 description 1
- 238000005809 transesterification reaction Methods 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 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
- C08G18/06—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
- C08G18/08—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)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Organic Chemistry (AREA)
- Polyurethanes Or Polyureas (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Polyesters Or Polycarbonates (AREA)
- Medicines Containing Antibodies Or Antigens For Use As Internal Diagnostic Agents (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19939840.2 | 1999-08-23 | ||
| DE19939840A DE19939840A1 (de) | 1999-08-23 | 1999-08-23 | Verfahren zur Herstellung von Isocyanatendgruppen enthaltenden Prepolymeren mit einem geringem Anteil an eingesetzten Ausgangsisocyanaten |
| PCT/EP2000/007823 WO2001014443A1 (de) | 1999-08-23 | 2000-08-11 | Verfahren zur herstellung von isocyanatendgruppen enthaltenden prepolymeren mit einem geringen anteil an eingesetzten ausgangsisocyanaten |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA2382031A1 true CA2382031A1 (en) | 2001-03-01 |
Family
ID=7919267
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA002382031A Abandoned CA2382031A1 (en) | 1999-08-23 | 2000-08-11 | Method for producing prepolymers containing isocyanate end groups, incorporating a small proportion of base isocyanates |
Country Status (19)
| Country | Link |
|---|---|
| US (1) | US6667370B1 (enExample) |
| EP (1) | EP1224233B1 (enExample) |
| JP (1) | JP2003507545A (enExample) |
| CN (1) | CN1146614C (enExample) |
| AT (1) | ATE253605T1 (enExample) |
| AU (1) | AU6994800A (enExample) |
| BR (1) | BR0013485A (enExample) |
| CA (1) | CA2382031A1 (enExample) |
| CZ (1) | CZ2002649A3 (enExample) |
| DE (2) | DE19939840A1 (enExample) |
| DK (1) | DK1224233T3 (enExample) |
| ES (1) | ES2209967T3 (enExample) |
| HK (1) | HK1047292A1 (enExample) |
| HU (1) | HUP0203200A3 (enExample) |
| MX (1) | MXPA02001948A (enExample) |
| PL (1) | PL364864A1 (enExample) |
| PT (1) | PT1224233E (enExample) |
| TR (1) | TR200200413T2 (enExample) |
| WO (1) | WO2001014443A1 (enExample) |
Families Citing this family (18)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| MXPA02002226A (es) * | 2001-03-14 | 2002-09-30 | Rohm & Haas | Metodo para preparar prepolimeros con funcionalidad de isocianato con baja concentracion de monomeros de isocianato residual. |
| EP1451239B1 (de) * | 2001-11-27 | 2008-04-02 | Basf Se | Verfahen zur herstellung von isocyanatgruppen und urethangruppen enthaltenden prepolymeren |
| DE102005035000A1 (de) | 2005-07-22 | 2007-01-25 | Basf Ag | Isocyanatgruppen enthaltende Prepolymere |
| EP1918314A1 (de) | 2006-10-31 | 2008-05-07 | Sika Technology AG | Polyurethanzusammensetzung mit guter Anfangsfestigkeit |
| EP1975187A1 (de) | 2007-03-28 | 2008-10-01 | Sika Technology AG | Verfahren zur Herstellung von Polyurethanzusammensetzungen mit niedrigem Isocyanat-Monomergehalt |
| PL2780384T5 (pl) | 2011-11-16 | 2020-11-02 | Soudal | Ulepszona kompozycja pianki poliuretanowej |
| EP2800834B1 (en) | 2012-01-04 | 2018-05-30 | Soudal | Filling of cavities in road construction and repair |
| RU2636015C2 (ru) | 2012-08-29 | 2017-11-17 | Судаль | Улучшенная оконная изоляция |
| US20140342110A1 (en) * | 2013-05-15 | 2014-11-20 | Chemtura Corporation | Thermoplastic Polyurethane From Low Free Monomer Prepolymer |
| WO2015135833A1 (de) | 2014-03-11 | 2015-09-17 | Sika Technology Ag | Polyurethan-heissschmelzklebstoff mit niedrigem gehalt an monomeren diisocyanaten und guter vernetzungsgeschwindigkeit |
| EP3088435A1 (de) | 2015-04-28 | 2016-11-02 | Sika Technology AG | Zweistufiges verfahren zur herstellung eines polyurethan-heissschmelzklebstoffs mit niedrigem gehalt an monomeren diisocyanaten und hoher anfangsfestigkeit |
| EP3315527B1 (en) | 2016-11-01 | 2021-05-05 | Sika Technology AG | Moisture curing hot-melt adhesive with low content of diisocyanate monomers, reduced rest tackiness and high thermal stability |
| PL3315528T3 (pl) | 2016-11-01 | 2022-03-07 | Sika Technology Ag | Sposób zmniejszania kleistości spoczynkowej termotopliwych klejów poliuretanowych utwardzanych wilgocią |
| CN108373528A (zh) * | 2017-02-01 | 2018-08-07 | 胡海东 | 一种复合材料基体树脂 |
| CA3121591A1 (en) | 2018-12-19 | 2020-06-25 | Covestro Llc | Process for manufacturing fully recyclable mining screens |
| PL4291588T3 (pl) | 2021-02-11 | 2025-12-08 | Basf Se | Zmniejszenie zawartości monomerowych izocyjanianów z użyciem porowatego materiału |
| CN117355551A (zh) * | 2021-06-24 | 2024-01-05 | Sika技术股份公司 | 降低聚氨酯组合物中单体多异氰酸酯的含量 |
| EP4551632A1 (en) | 2022-07-04 | 2025-05-14 | Sika Technology AG | Reactive hot-melt adhesive having low content of monomeric diisocyanates |
Family Cites Families (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4543405A (en) * | 1984-10-01 | 1985-09-24 | Ppg Industries, Inc. | High solids polyurethane polyols and coating compositions thereof |
| US4568717A (en) * | 1984-10-09 | 1986-02-04 | Texaco, Inc. | Polymer polyols from liquid terephthalic polyester polyols |
| US4786703A (en) * | 1987-04-15 | 1988-11-22 | Air Products And Chemicals, Inc. | Process for the preparation of polyisocyanate prepolymers and polyurethanes having high temperature performance and low hysteresis |
| DE4223014A1 (de) * | 1992-07-13 | 1994-01-20 | Bayer Ag | Verfahren zur Herstellung foggingarmer Polyesterpolyurethane-Weichschaumstoffe und ihre Verwendung in Verkehrsmitteln |
| DE19601410B4 (de) * | 1996-01-17 | 2004-12-09 | Basf Ag | Verfahren zur Herstellung von Polyurethanweichschaumstoffen |
-
1999
- 1999-08-23 DE DE19939840A patent/DE19939840A1/de not_active Withdrawn
-
2000
- 2000-08-11 ES ES00958423T patent/ES2209967T3/es not_active Expired - Lifetime
- 2000-08-11 DK DK00958423T patent/DK1224233T3/da active
- 2000-08-11 WO PCT/EP2000/007823 patent/WO2001014443A1/de not_active Ceased
- 2000-08-11 PL PL00364864A patent/PL364864A1/xx not_active Application Discontinuation
- 2000-08-11 HU HU0203200A patent/HUP0203200A3/hu unknown
- 2000-08-11 AT AT00958423T patent/ATE253605T1/de not_active IP Right Cessation
- 2000-08-11 CN CNB008119716A patent/CN1146614C/zh not_active Expired - Fee Related
- 2000-08-11 US US10/049,926 patent/US6667370B1/en not_active Expired - Fee Related
- 2000-08-11 PT PT00958423T patent/PT1224233E/pt unknown
- 2000-08-11 AU AU69948/00A patent/AU6994800A/en not_active Abandoned
- 2000-08-11 TR TR2002/00413T patent/TR200200413T2/xx unknown
- 2000-08-11 BR BR0013485-6A patent/BR0013485A/pt not_active Application Discontinuation
- 2000-08-11 JP JP2001518771A patent/JP2003507545A/ja active Pending
- 2000-08-11 CZ CZ2002649A patent/CZ2002649A3/cs unknown
- 2000-08-11 MX MXPA02001948A patent/MXPA02001948A/es not_active Application Discontinuation
- 2000-08-11 CA CA002382031A patent/CA2382031A1/en not_active Abandoned
- 2000-08-11 DE DE50004367T patent/DE50004367D1/de not_active Expired - Fee Related
- 2000-08-11 HK HK02108965.2A patent/HK1047292A1/zh unknown
- 2000-08-11 EP EP00958423A patent/EP1224233B1/de not_active Expired - Lifetime
Also Published As
| Publication number | Publication date |
|---|---|
| BR0013485A (pt) | 2002-05-07 |
| DK1224233T3 (da) | 2004-02-09 |
| EP1224233B1 (de) | 2003-11-05 |
| CZ2002649A3 (cs) | 2002-06-12 |
| EP1224233A1 (de) | 2002-07-24 |
| WO2001014443A1 (de) | 2001-03-01 |
| JP2003507545A (ja) | 2003-02-25 |
| TR200200413T2 (tr) | 2002-11-21 |
| PT1224233E (pt) | 2004-03-31 |
| ATE253605T1 (de) | 2003-11-15 |
| CN1371396A (zh) | 2002-09-25 |
| ES2209967T3 (es) | 2004-07-01 |
| MXPA02001948A (es) | 2002-10-31 |
| CN1146614C (zh) | 2004-04-21 |
| PL364864A1 (en) | 2004-12-27 |
| US6667370B1 (en) | 2003-12-23 |
| HUP0203200A3 (en) | 2003-09-29 |
| DE19939840A1 (de) | 2001-03-01 |
| AU6994800A (en) | 2001-03-19 |
| HK1047292A1 (zh) | 2003-02-14 |
| HUP0203200A2 (hu) | 2003-01-28 |
| DE50004367D1 (de) | 2003-12-11 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| FZDE | Discontinued |