CA1038542A - Cure of polyurethanes with mixed curatives - Google Patents
Cure of polyurethanes with mixed curativesInfo
- Publication number
- CA1038542A CA1038542A CA210,119A CA210119A CA1038542A CA 1038542 A CA1038542 A CA 1038542A CA 210119 A CA210119 A CA 210119A CA 1038542 A CA1038542 A CA 1038542A
- Authority
- CA
- Canada
- Prior art keywords
- plus
- ratio
- weight
- prepolymer
- curative
- 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
- 239000004814 polyurethane Substances 0.000 title description 10
- 229920002635 polyurethane Polymers 0.000 title description 9
- WERYXYBDKMZEQL-UHFFFAOYSA-N butane-1,4-diol Chemical compound OCCCCO WERYXYBDKMZEQL-UHFFFAOYSA-N 0.000 claims abstract description 26
- 239000000203 mixture Substances 0.000 claims abstract description 16
- OJPDDQSCZGTACX-UHFFFAOYSA-N 2-[n-(2-hydroxyethyl)anilino]ethanol Chemical compound OCCN(CCO)C1=CC=CC=C1 OJPDDQSCZGTACX-UHFFFAOYSA-N 0.000 claims abstract description 8
- 229920001730 Moisture cure polyurethane Polymers 0.000 claims abstract description 7
- WTPYFJNYAMXZJG-UHFFFAOYSA-N 2-[4-(2-hydroxyethoxy)phenoxy]ethanol Chemical compound OCCOC1=CC=C(OCCO)C=C1 WTPYFJNYAMXZJG-UHFFFAOYSA-N 0.000 claims abstract description 6
- 230000000704 physical effect Effects 0.000 claims abstract description 3
- SLINHMUFWFWBMU-UHFFFAOYSA-N Triisopropanolamine Chemical compound CC(O)CN(CC(C)O)CC(C)O SLINHMUFWFWBMU-UHFFFAOYSA-N 0.000 claims abstract 3
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 claims description 33
- 238000000034 method Methods 0.000 claims description 15
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 claims description 13
- -1 polytetramethylene Polymers 0.000 claims description 10
- 229920000728 polyester Polymers 0.000 claims description 9
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 8
- 239000012948 isocyanate Substances 0.000 claims description 6
- 150000002513 isocyanates Chemical class 0.000 claims description 6
- 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 claims description 5
- 239000007788 liquid Substances 0.000 claims description 5
- IQPQWNKOIGAROB-UHFFFAOYSA-N isocyanate group Chemical group [N-]=C=O IQPQWNKOIGAROB-UHFFFAOYSA-N 0.000 claims description 4
- 239000007795 chemical reaction product Substances 0.000 claims description 3
- 239000001361 adipic acid Substances 0.000 claims description 2
- 239000000047 product Substances 0.000 claims description 2
- 238000004519 manufacturing process Methods 0.000 claims 1
- 238000000465 moulding Methods 0.000 abstract 1
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 10
- 229920000570 polyether Polymers 0.000 description 8
- 239000004721 Polyphenylene oxide Substances 0.000 description 7
- 150000001412 amines Chemical class 0.000 description 5
- 125000005442 diisocyanate group Chemical group 0.000 description 5
- 150000002334 glycols Chemical class 0.000 description 4
- 229920000642 polymer Polymers 0.000 description 4
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 description 3
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 3
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 3
- 239000002253 acid Substances 0.000 description 3
- 229910052739 hydrogen Inorganic materials 0.000 description 3
- 239000001257 hydrogen Substances 0.000 description 3
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 3
- 229920001228 polyisocyanate Polymers 0.000 description 3
- 239000005056 polyisocyanate Substances 0.000 description 3
- 239000005977 Ethylene Substances 0.000 description 2
- QIGBRXMKCJKVMJ-UHFFFAOYSA-N Hydroquinone Chemical compound OC1=CC=C(O)C=C1 QIGBRXMKCJKVMJ-UHFFFAOYSA-N 0.000 description 2
- WNLRTRBMVRJNCN-UHFFFAOYSA-N adipic acid Chemical compound OC(=O)CCCCC(O)=O WNLRTRBMVRJNCN-UHFFFAOYSA-N 0.000 description 2
- 229910052799 carbon Inorganic materials 0.000 description 2
- 238000006243 chemical reaction Methods 0.000 description 2
- 239000003795 chemical substances by application Substances 0.000 description 2
- 150000001875 compounds Chemical class 0.000 description 2
- 238000005336 cracking Methods 0.000 description 2
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 2
- 239000000463 material Substances 0.000 description 2
- YPFDHNVEDLHUCE-UHFFFAOYSA-N propane-1,3-diol Chemical compound OCCCO YPFDHNVEDLHUCE-UHFFFAOYSA-N 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- 125000001989 1,3-phenylene group Chemical group [H]C1=C([H])C([*:1])=C([H])C([*:2])=C1[H] 0.000 description 1
- ALQLPWJFHRMHIU-UHFFFAOYSA-N 1,4-diisocyanatobenzene Chemical class O=C=NC1=CC=C(N=C=O)C=C1 ALQLPWJFHRMHIU-UHFFFAOYSA-N 0.000 description 1
- SBJCUZQNHOLYMD-UHFFFAOYSA-N 1,5-Naphthalene diisocyanate Chemical compound C1=CC=C2C(N=C=O)=CC=CC2=C1N=C=O SBJCUZQNHOLYMD-UHFFFAOYSA-N 0.000 description 1
- 241000219498 Alnus glutinosa Species 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- 239000004606 Fillers/Extenders Substances 0.000 description 1
- 241001274660 Modulus Species 0.000 description 1
- ZJCCRDAZUWHFQH-UHFFFAOYSA-N Trimethylolpropane Chemical compound CCC(CO)(CO)CO ZJCCRDAZUWHFQH-UHFFFAOYSA-N 0.000 description 1
- 238000007259 addition reaction Methods 0.000 description 1
- 235000011037 adipic acid Nutrition 0.000 description 1
- 125000004429 atom Chemical group 0.000 description 1
- 238000005452 bending Methods 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- OMWQUXGVXQELIX-UHFFFAOYSA-N bitoscanate Chemical compound S=C=NC1=CC=C(N=C=S)C=C1 OMWQUXGVXQELIX-UHFFFAOYSA-N 0.000 description 1
- 125000004432 carbon atom Chemical group C* 0.000 description 1
- 150000004985 diamines Chemical class 0.000 description 1
- 150000001991 dicarboxylic acids Chemical class 0.000 description 1
- 229920001971 elastomer Polymers 0.000 description 1
- 239000000806 elastomer Substances 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 239000004744 fabric Substances 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 229960004337 hydroquinone Drugs 0.000 description 1
- 230000007775 late Effects 0.000 description 1
- 150000002894 organic compounds Chemical class 0.000 description 1
- JTJMJGYZQZDUJJ-UHFFFAOYSA-N phencyclidine Chemical compound C1CCCCN1C1(C=2C=CC=CC=2)CCCCC1 JTJMJGYZQZDUJJ-UHFFFAOYSA-N 0.000 description 1
- 229920000921 polyethylene adipate Polymers 0.000 description 1
- 229920001451 polypropylene glycol Polymers 0.000 description 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 229940116351 sebacate Drugs 0.000 description 1
- CXMXRPHRNRROMY-UHFFFAOYSA-L sebacate(2-) Chemical compound [O-]C(=O)CCCCCCCCC([O-])=O CXMXRPHRNRROMY-UHFFFAOYSA-L 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 235000012976 tarts Nutrition 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
- QXJQHYBHAIHNGG-UHFFFAOYSA-N trimethylolethane Chemical compound OCC(C)(CO)CO QXJQHYBHAIHNGG-UHFFFAOYSA-N 0.000 description 1
- JOYRKODLDBILNP-UHFFFAOYSA-N urethane group Chemical group NC(=O)OCC JOYRKODLDBILNP-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
- C08G18/08—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)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US454646A US3892713A (en) | 1974-03-25 | 1974-03-25 | Cure of polyurethanes with mixed curatives comprising hydroxy tertiary amines |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA1038542A true CA1038542A (en) | 1978-09-12 |
Family
ID=23805484
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA210,119A Expired CA1038542A (en) | 1974-03-25 | 1974-09-26 | Cure of polyurethanes with mixed curatives |
Country Status (10)
| Country | Link |
|---|---|
| US (1) | US3892713A (OSRAM) |
| JP (1) | JPS583489B2 (OSRAM) |
| BE (1) | BE826864A (OSRAM) |
| CA (1) | CA1038542A (OSRAM) |
| DE (1) | DE2513205C2 (OSRAM) |
| FR (1) | FR2265785B1 (OSRAM) |
| GB (1) | GB1491936A (OSRAM) |
| IT (1) | IT1030319B (OSRAM) |
| NL (1) | NL7502241A (OSRAM) |
| ZA (1) | ZA75898B (OSRAM) |
Families Citing this family (11)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4267299A (en) * | 1978-09-22 | 1981-05-12 | Metalweld, Inc. | Method of curing isocyanate-terminated polyurethane prepolymers for use in solventless spray applications |
| DE3411361A1 (de) * | 1984-03-28 | 1985-10-10 | Akzo Gmbh, 5600 Wuppertal | Einbettmaterial, verfahren zu seiner herstellung und seine verwendung |
| US4738999A (en) * | 1986-03-31 | 1988-04-19 | Lord Corporation | Fiber reinforced composites |
| US4916200A (en) * | 1987-06-08 | 1990-04-10 | Dow Corning Corporation | Silane modified polysilacyclobutasilazanes |
| US4929742A (en) * | 1988-11-28 | 1990-05-29 | Dow Corning Corporation | Silane modified polysilacyclobutasilazanes |
| TW264487B (OSRAM) * | 1992-02-18 | 1995-12-01 | Takeda Pharm Industry Co Ltd | |
| US5551197A (en) | 1993-09-30 | 1996-09-03 | Donnelly Corporation | Flush-mounted articulated/hinged window assembly |
| CA2214827A1 (en) * | 1995-03-28 | 1996-10-03 | Uniroyal Chemical Company, Inc. | Polyurethane curative systems and elastomers |
| US7838115B2 (en) | 1995-04-11 | 2010-11-23 | Magna Mirrors Of America, Inc. | Method for manufacturing an articulatable vehicular window assembly |
| US5840233A (en) | 1997-09-16 | 1998-11-24 | Optimer, Inc. | Process of making melt-spun elastomeric fibers |
| US6780908B1 (en) | 2000-06-21 | 2004-08-24 | E. I. Du Pont De Nemours And Company | Coating composition |
Family Cites Families (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3044971A (en) * | 1959-03-18 | 1962-07-17 | Mobay Chemical Corp | Polyurethane catalyst composition and method for preparing cellular polyurethane using same |
| US3476933A (en) * | 1966-10-21 | 1969-11-04 | Westinghouse Electric Corp | Large-celled polyurethane foam |
-
1974
- 1974-03-25 US US454646A patent/US3892713A/en not_active Expired - Lifetime
- 1974-09-26 CA CA210,119A patent/CA1038542A/en not_active Expired
-
1975
- 1975-02-12 ZA ZA00750898A patent/ZA75898B/xx unknown
- 1975-02-25 NL NL7502241A patent/NL7502241A/xx not_active Application Discontinuation
- 1975-03-11 IT IT67614/75A patent/IT1030319B/it active
- 1975-03-19 BE BE154486A patent/BE826864A/xx unknown
- 1975-03-21 GB GB11957/75A patent/GB1491936A/en not_active Expired
- 1975-03-24 JP JP50035281A patent/JPS583489B2/ja not_active Expired
- 1975-03-24 FR FR7509156A patent/FR2265785B1/fr not_active Expired
- 1975-03-25 DE DE2513205A patent/DE2513205C2/de not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| JPS50129696A (OSRAM) | 1975-10-14 |
| US3892713A (en) | 1975-07-01 |
| BE826864A (fr) | 1975-09-19 |
| IT1030319B (it) | 1979-03-30 |
| FR2265785B1 (OSRAM) | 1979-02-23 |
| ZA75898B (en) | 1976-01-28 |
| DE2513205A1 (de) | 1975-10-09 |
| NL7502241A (nl) | 1975-09-29 |
| FR2265785A1 (OSRAM) | 1975-10-24 |
| DE2513205C2 (de) | 1986-01-09 |
| JPS583489B2 (ja) | 1983-01-21 |
| GB1491936A (en) | 1977-11-16 |
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