GB1040365A - Improvements in or relating to the manufacture of synthetic polyurethane elastomers - Google Patents
Improvements in or relating to the manufacture of synthetic polyurethane elastomersInfo
- Publication number
- GB1040365A GB1040365A GB7233/64A GB723364A GB1040365A GB 1040365 A GB1040365 A GB 1040365A GB 7233/64 A GB7233/64 A GB 7233/64A GB 723364 A GB723364 A GB 723364A GB 1040365 A GB1040365 A GB 1040365A
- Authority
- GB
- United Kingdom
- Prior art keywords
- diol
- trans
- aliphatic
- moles
- isocyanato
- 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
- 238000004519 manufacturing process Methods 0.000 title 1
- 229920003225 polyurethane elastomer Polymers 0.000 title 1
- 150000002009 diols Chemical class 0.000 abstract 5
- -1 aromatic dicarboxylic acids Chemical class 0.000 abstract 4
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 abstract 3
- 125000005442 diisocyanate group Chemical group 0.000 abstract 3
- 229920001634 Copolyester Polymers 0.000 abstract 2
- ATUOYWHBWRKTHZ-UHFFFAOYSA-N Propane Chemical compound CCC ATUOYWHBWRKTHZ-UHFFFAOYSA-N 0.000 abstract 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 abstract 2
- WNLRTRBMVRJNCN-UHFFFAOYSA-N adipic acid Chemical compound OC(=O)CCCCC(O)=O WNLRTRBMVRJNCN-UHFFFAOYSA-N 0.000 abstract 2
- 125000001931 aliphatic group Chemical group 0.000 abstract 2
- 125000000732 arylene group Chemical group 0.000 abstract 2
- 125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 abstract 2
- PUPZLCDOIYMWBV-UHFFFAOYSA-N (+/-)-1,3-Butanediol Chemical compound CC(O)CCO PUPZLCDOIYMWBV-UHFFFAOYSA-N 0.000 abstract 1
- OHLKMGYGBHFODF-UHFFFAOYSA-N 1,4-bis(isocyanatomethyl)benzene Chemical class O=C=NCC1=CC=C(CN=C=O)C=C1 OHLKMGYGBHFODF-UHFFFAOYSA-N 0.000 abstract 1
- CDMDQYCEEKCBGR-UHFFFAOYSA-N 1,4-diisocyanatocyclohexane Chemical compound O=C=NC1CCC(N=C=O)CC1 CDMDQYCEEKCBGR-UHFFFAOYSA-N 0.000 abstract 1
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 abstract 1
- NTIZESTWPVYFNL-UHFFFAOYSA-N Methyl isobutyl ketone Chemical compound CC(C)CC(C)=O NTIZESTWPVYFNL-UHFFFAOYSA-N 0.000 abstract 1
- UIHCLUNTQKBZGK-UHFFFAOYSA-N Methyl isobutyl ketone Natural products CCC(C)C(C)=O UIHCLUNTQKBZGK-UHFFFAOYSA-N 0.000 abstract 1
- FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 abstract 1
- KORSJDCBLAPZEQ-KTSLABGISA-N O=C=N[C@H]1CC[C@H](C[C@H]2CC[C@@H](CC2)N=C=O)CC1 Chemical compound O=C=N[C@H]1CC[C@H](C[C@H]2CC[C@@H](CC2)N=C=O)CC1 KORSJDCBLAPZEQ-KTSLABGISA-N 0.000 abstract 1
- 229920006311 Urethane elastomer Polymers 0.000 abstract 1
- 235000011037 adipic acid Nutrition 0.000 abstract 1
- 239000001361 adipic acid Substances 0.000 abstract 1
- 150000001991 dicarboxylic acids Chemical class 0.000 abstract 1
- 229960001760 dimethyl sulfoxide Drugs 0.000 abstract 1
- 230000032050 esterification Effects 0.000 abstract 1
- 238000005886 esterification reaction Methods 0.000 abstract 1
- 150000002334 glycols Chemical class 0.000 abstract 1
- GNOIPBMMFNIUFM-UHFFFAOYSA-N hexamethylphosphoric triamide Chemical compound CN(C)P(=O)(N(C)C)N(C)C GNOIPBMMFNIUFM-UHFFFAOYSA-N 0.000 abstract 1
- 238000000034 method Methods 0.000 abstract 1
- 229940043265 methyl isobutyl ketone Drugs 0.000 abstract 1
- 229920000728 polyester Polymers 0.000 abstract 1
- 239000001294 propane Substances 0.000 abstract 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 abstract 1
- HXJUTPCZVOIRIF-UHFFFAOYSA-N sulfolane Chemical compound O=S1(=O)CCCC1 HXJUTPCZVOIRIF-UHFFFAOYSA-N 0.000 abstract 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
- C08G18/70—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
-
- 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
-
- 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
- C08G18/65—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
- C08G18/6633—Compounds of group C08G18/42
- C08G18/6637—Compounds of group C08G18/42 with compounds of group C08G18/32 or polyamines of C08G18/38
- C08G18/664—Compounds of group C08G18/42 with compounds of group C08G18/32 or polyamines of C08G18/38 with compounds of group C08G18/3203
-
- 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
- C08G18/73—Polyisocyanates or polyisothiocyanates acyclic
-
- 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
-
- D—TEXTILES; PAPER
- D01—NATURAL OR MAN-MADE THREADS OR FIBRES; SPINNING
- D01F—CHEMICAL FEATURES IN THE MANUFACTURE OF ARTIFICIAL FILAMENTS, THREADS, FIBRES, BRISTLES OR RIBBONS; APPARATUS SPECIALLY ADAPTED FOR THE MANUFACTURE OF CARBON FILAMENTS
- D01F6/00—Monocomponent artificial filaments or the like of synthetic polymers; Manufacture thereof
- D01F6/58—Monocomponent artificial filaments or the like of synthetic polymers; Manufacture thereof from homopolycondensation products
- D01F6/72—Monocomponent artificial filaments or the like of synthetic polymers; Manufacture thereof from homopolycondensation products from polyureas
-
- D—TEXTILES; PAPER
- D01—NATURAL OR MAN-MADE THREADS OR FIBRES; SPINNING
- D01F—CHEMICAL FEATURES IN THE MANUFACTURE OF ARTIFICIAL FILAMENTS, THREADS, FIBRES, BRISTLES OR RIBBONS; APPARATUS SPECIALLY ADAPTED FOR THE MANUFACTURE OF CARBON FILAMENTS
- D01F6/00—Monocomponent artificial filaments or the like of synthetic polymers; Manufacture thereof
- D01F6/88—Monocomponent artificial filaments or the like of synthetic polymers; Manufacture thereof from mixtures of polycondensation products as major constituent with other polymers or low-molecular-weight compounds
- D01F6/92—Monocomponent artificial filaments or the like of synthetic polymers; Manufacture thereof from mixtures of polycondensation products as major constituent with other polymers or low-molecular-weight compounds of polyesters
Abstract
Polyester urethane elastomers are prepared by reacting (1) a linear copolyester diol of average M.W. 1500-3500 derivable by a process of esterification from one or more aliphatic or cycloaliphatic glycols having 2-20 C, and adipic acid, optionally together with one or more other dicarboxylic acids selected from saturated aliphatic and aromatic dicarboxylic acids, (2) from 2-20 moles, per mole of copolyester diol, of an aliphatic diol optionally containing arylene groups separated from the -OH groups by at least one methylene group or a cycloaliphatic diol, which diol has not more than 20 C and (3) from 96-100 moles, per 100 moles of the foregoing diols, of an aliphatic diisocyanate which may optionally contain arylene groups separated from the -NCO groups by at least one methylene group, or a cycloaliphatic diisocyanate, said diisocyanate having 4-24 C. Diisocyanates specified are: trans-1,4-diisocyanato cyclohexane, trans-1,4-bis-isocyanato methyl cyclohexane, 2,2 - di - (41 - isocyanato-cyclohexyl) propane, trans,trans-di-(4-isocyanato - cyclohexyl) methane and hexamethylene-, tetramethylene-, pentamethylene, decamethylene, m-xylylene-, and p-xylylene diisocyanates. The polyesterurethane may be formed in solution, e.g. pyridine, N,N-dimethylacetamide, dimethylsulphoxide mixed with methyl-isobutylketone, N,N - dimethylformamide, hexamethylphosphoramide and tetramethylene sulphone.
Priority Applications (8)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB7233/64A GB1040365A (en) | 1964-02-20 | 1964-02-20 | Improvements in or relating to the manufacture of synthetic polyurethane elastomers |
| US429646A US3357954A (en) | 1964-02-20 | 1965-02-01 | Synthetic elastomeric filaments from (a) polyester diols, (b) aliphatic or cycloaliphatic diols and (c) aliphatic or cycloaliphatic diisocyanates |
| NL6501927A NL6501927A (en) | 1964-02-20 | 1965-02-16 | |
| LU47993A LU47993A1 (en) | 1964-02-20 | 1965-02-16 | |
| BE659935D BE659935A (en) | 1964-02-20 | 1965-02-18 | |
| CH228365A CH454456A (en) | 1964-02-20 | 1965-02-19 | Process for the production of polyester urethane elastomers and their use for melt spinning of non-yellowing elastic filaments |
| FR6350A FR1431138A (en) | 1964-02-20 | 1965-02-19 | Improvements in the manufacture of synthetic elastomers of polyesters |
| DE19651570241 DE1570241B2 (en) | 1964-02-20 | 1965-02-19 | METHOD FOR MANUFACTURING POLYESTERURETHANE ELASTOMERS |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB7233/64A GB1040365A (en) | 1964-02-20 | 1964-02-20 | Improvements in or relating to the manufacture of synthetic polyurethane elastomers |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB1040365A true GB1040365A (en) | 1966-08-24 |
Family
ID=9829200
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB7233/64A Expired GB1040365A (en) | 1964-02-20 | 1964-02-20 | Improvements in or relating to the manufacture of synthetic polyurethane elastomers |
Country Status (7)
| Country | Link |
|---|---|
| US (1) | US3357954A (en) |
| BE (1) | BE659935A (en) |
| CH (1) | CH454456A (en) |
| DE (1) | DE1570241B2 (en) |
| GB (1) | GB1040365A (en) |
| LU (1) | LU47993A1 (en) |
| NL (1) | NL6501927A (en) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4106313A (en) | 1968-11-06 | 1978-08-15 | Monsanto Company | Sheer stretch hose having high compressive force uniformity, and yarn |
Families Citing this family (21)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3669934A (en) * | 1964-05-26 | 1972-06-13 | Celanese Corp | Improved elastomeric fibers |
| NL130123C (en) * | 1965-07-28 | Rhone Poulenc Sa | ||
| DE1669403C3 (en) * | 1966-03-31 | 1974-02-07 | Bayer Ag, 5090 Leverkusen | Use of polyester amides for the production of monofilaments |
| US3436361A (en) * | 1966-06-09 | 1969-04-01 | Allied Chem | Quick drying urethane coatings |
| US3499869A (en) * | 1967-07-28 | 1970-03-10 | Eastman Kodak Co | Light stable polyurethane |
| GB1192390A (en) * | 1967-08-11 | 1970-05-20 | Ici Ltd | Polyurethanes |
| JPS4829558B1 (en) * | 1969-02-13 | 1973-09-11 | ||
| GB1313741A (en) * | 1969-05-15 | 1973-04-18 | Ici Ltd | Thermally reversible polymers |
| US3870683A (en) * | 1970-11-12 | 1975-03-11 | Gulf Oil Canada Ltd | Light stable polyurethanes based on dicyclohexyl and diisocyanates |
| US3987141A (en) * | 1973-04-20 | 1976-10-19 | Monsanto Company | Process for spinning polyurethane-hard polymer conjugate yarn |
| US3966866A (en) * | 1973-09-26 | 1976-06-29 | Monsanto Company | Polyurethane fiber uniformity |
| DE2432090C2 (en) * | 1974-07-04 | 1982-02-11 | Fa. Carl Freudenberg, 6940 Weinheim | Elastic molding compound based on polyurethane |
| US4051111A (en) * | 1976-08-20 | 1977-09-27 | The B. F. Goodrich Company | Injection moldable polyurethanes |
| US4393186A (en) * | 1979-06-19 | 1983-07-12 | Lord Corporation | Thermoplastic polyurethanes prepared by reacting polyisocyanate, polyester polyol, cycloaliphatic diol and a monofunctional chain-terminating compound |
| US4467595A (en) * | 1980-08-18 | 1984-08-28 | Akzona Incorporated | Latent contractable elastomers, composite yarns therefrom and methods of formation and use |
| US4554121A (en) * | 1980-08-18 | 1985-11-19 | Akzona Incorporated | Method of forming latent-contractable elastomeric composite yarns |
| DE3233384A1 (en) * | 1982-09-08 | 1984-03-08 | Akzo Gmbh, 5600 Wuppertal | THERMOPLASTIC POLYURETHANE ELASTOMERS MADE FROM CYCLOHEXANE-1.4-DIISOCYANATE |
| DE3717070A1 (en) * | 1987-05-21 | 1988-12-08 | Bayer Ag | POLYESTER POLYURETHANES AND THEIR USE AS ADHESIVE |
| US4877856A (en) * | 1987-08-31 | 1989-10-31 | The Bf Goodrich Company | Soft thermoplastic polyurethane for blown film application |
| US6017997A (en) * | 1997-10-31 | 2000-01-25 | The B. F. Goodrich Company | Waterborne polyurethane having film properties comparable to rubber |
| WO2015052853A1 (en) * | 2013-10-10 | 2015-04-16 | Panasonic Intellectual Property Management Co., Ltd. | Resin composition and film using same |
Family Cites Families (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2871218A (en) * | 1955-12-01 | 1959-01-27 | Goodrich Co B F | Simulated vulcanizates of polyurethane elastomers |
| NL281045A (en) * | 1961-07-18 | |||
| US3233025A (en) * | 1962-04-24 | 1966-02-01 | Mobay Chemical Corp | Method of making polyurethanes |
-
1964
- 1964-02-20 GB GB7233/64A patent/GB1040365A/en not_active Expired
-
1965
- 1965-02-01 US US429646A patent/US3357954A/en not_active Expired - Lifetime
- 1965-02-16 LU LU47993A patent/LU47993A1/xx unknown
- 1965-02-16 NL NL6501927A patent/NL6501927A/xx unknown
- 1965-02-18 BE BE659935D patent/BE659935A/xx unknown
- 1965-02-19 CH CH228365A patent/CH454456A/en unknown
- 1965-02-19 DE DE19651570241 patent/DE1570241B2/en active Pending
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4106313A (en) | 1968-11-06 | 1978-08-15 | Monsanto Company | Sheer stretch hose having high compressive force uniformity, and yarn |
Also Published As
| Publication number | Publication date |
|---|---|
| US3357954A (en) | 1967-12-12 |
| DE1570241B2 (en) | 1972-02-24 |
| BE659935A (en) | 1965-08-18 |
| LU47993A1 (en) | 1965-04-16 |
| DE1570241A1 (en) | 1970-02-12 |
| NL6501927A (en) | 1965-08-23 |
| CH454456A (en) | 1968-04-15 |
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