CA1114991A - Injection moldable polyurethanes - Google Patents
Injection moldable polyurethanesInfo
- Publication number
- CA1114991A CA1114991A CA285,078A CA285078A CA1114991A CA 1114991 A CA1114991 A CA 1114991A CA 285078 A CA285078 A CA 285078A CA 1114991 A CA1114991 A CA 1114991A
- Authority
- CA
- Canada
- Prior art keywords
- polyurethane
- molecular weight
- less
- diisocyanate
- hydroxyl
- 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 claims abstract description 36
- 229920002635 polyurethane Polymers 0.000 title claims abstract description 34
- 238000002347 injection Methods 0.000 title abstract description 9
- 239000007924 injection Substances 0.000 title abstract description 9
- 229920000728 polyester Polymers 0.000 claims abstract description 24
- 238000006243 chemical reaction Methods 0.000 claims abstract description 21
- PUPZLCDOIYMWBV-UHFFFAOYSA-N (+/-)-1,3-Butanediol Chemical compound CC(O)CCO PUPZLCDOIYMWBV-UHFFFAOYSA-N 0.000 claims abstract description 8
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 claims description 20
- -1 poly(tetramethylene) Polymers 0.000 claims description 15
- 239000000203 mixture Substances 0.000 claims description 14
- 125000005442 diisocyanate group Chemical group 0.000 claims description 12
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 claims description 10
- 239000000376 reactant Substances 0.000 claims description 10
- 125000004432 carbon atom Chemical group C* 0.000 claims description 8
- 150000002009 diols Chemical class 0.000 claims description 8
- 125000001931 aliphatic group Chemical group 0.000 claims description 7
- WERYXYBDKMZEQL-UHFFFAOYSA-N butane-1,4-diol Chemical compound OCCCCO WERYXYBDKMZEQL-UHFFFAOYSA-N 0.000 claims description 7
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 6
- UPMLOUAZCHDJJD-UHFFFAOYSA-N 4,4'-Diphenylmethane Diisocyanate Chemical group C1=CC(N=C=O)=CC=C1CC1=CC=C(N=C=O)C=C1 UPMLOUAZCHDJJD-UHFFFAOYSA-N 0.000 claims description 5
- WNLRTRBMVRJNCN-UHFFFAOYSA-L adipate(2-) Chemical compound [O-]C(=O)CCCCC([O-])=O WNLRTRBMVRJNCN-UHFFFAOYSA-L 0.000 claims description 3
- 150000002148 esters Chemical class 0.000 claims description 3
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 2
- OFOBLEOULBTSOW-UHFFFAOYSA-N Malonic acid Chemical compound OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 claims 1
- 230000000704 physical effect Effects 0.000 abstract description 12
- 238000001746 injection moulding Methods 0.000 abstract description 6
- 230000003247 decreasing effect Effects 0.000 abstract 1
- 229920000642 polymer Polymers 0.000 description 10
- 238000010438 heat treatment Methods 0.000 description 7
- 239000004433 Thermoplastic polyurethane Substances 0.000 description 6
- 150000002596 lactones Chemical group 0.000 description 5
- 239000000463 material Substances 0.000 description 5
- 229920002803 thermoplastic polyurethane Polymers 0.000 description 5
- 239000000047 product Substances 0.000 description 4
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 3
- 125000003118 aryl group Chemical group 0.000 description 3
- 230000001588 bifunctional effect Effects 0.000 description 3
- 150000001875 compounds Chemical class 0.000 description 3
- 229910052739 hydrogen Inorganic materials 0.000 description 3
- 239000001257 hydrogen Substances 0.000 description 3
- 206010037660 Pyrexia Diseases 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- 125000000217 alkyl group Chemical group 0.000 description 2
- 150000001414 amino alcohols Chemical class 0.000 description 2
- CDQSJQSWAWPGKG-UHFFFAOYSA-N butane-1,1-diol Chemical compound CCCC(O)O CDQSJQSWAWPGKG-UHFFFAOYSA-N 0.000 description 2
- 150000004985 diamines Chemical class 0.000 description 2
- XXMIOPMDWAUFGU-UHFFFAOYSA-N hexane-1,6-diol Chemical compound OCCCCCCO XXMIOPMDWAUFGU-UHFFFAOYSA-N 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- 238000002844 melting Methods 0.000 description 2
- 230000008018 melting Effects 0.000 description 2
- 229910052760 oxygen Inorganic materials 0.000 description 2
- 239000003973 paint Substances 0.000 description 2
- 229920001610 polycaprolactone Polymers 0.000 description 2
- 238000006116 polymerization reaction Methods 0.000 description 2
- 238000002360 preparation method Methods 0.000 description 2
- 239000011541 reaction mixture Substances 0.000 description 2
- 239000007787 solid Substances 0.000 description 2
- 238000005303 weighing Methods 0.000 description 2
- ALQLPWJFHRMHIU-UHFFFAOYSA-N 1,4-diisocyanatobenzene Chemical compound O=C=NC1=CC=C(N=C=O)C=C1 ALQLPWJFHRMHIU-UHFFFAOYSA-N 0.000 description 1
- XXCRXPYEAMCJKH-UHFFFAOYSA-N 3,3,4-trimethyloxepan-2-one Chemical compound CC1CCCOC(=O)C1(C)C XXCRXPYEAMCJKH-UHFFFAOYSA-N 0.000 description 1
- LROFMHLJBOIJHA-UHFFFAOYSA-N 3,3-dimethyloxepan-2-one Chemical compound CC1(C)CCCCOC1=O LROFMHLJBOIJHA-UHFFFAOYSA-N 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- 239000004215 Carbon black (E152) Substances 0.000 description 1
- 239000005058 Isophorone diisocyanate Substances 0.000 description 1
- INWVTRVMRQMCCM-UHFFFAOYSA-N N=C=O.N=C=O.C=1C=CC=CC=1C(C)(C)C1=CC=CC=C1 Chemical compound N=C=O.N=C=O.C=1C=CC=CC=1C(C)(C)C1=CC=CC=C1 INWVTRVMRQMCCM-UHFFFAOYSA-N 0.000 description 1
- WMTLVUCMBWBYSO-UHFFFAOYSA-N N=C=O.N=C=O.C=1C=CC=CC=1OC1=CC=CC=C1 Chemical class N=C=O.N=C=O.C=1C=CC=CC=1OC1=CC=CC=C1 WMTLVUCMBWBYSO-UHFFFAOYSA-N 0.000 description 1
- RSPISYXLHRIGJD-UHFFFAOYSA-N OOOO Chemical compound OOOO RSPISYXLHRIGJD-UHFFFAOYSA-N 0.000 description 1
- KUGRPPRAQNPSQD-UHFFFAOYSA-N OOOOO Chemical compound OOOOO KUGRPPRAQNPSQD-UHFFFAOYSA-N 0.000 description 1
- 239000004721 Polyphenylene oxide Substances 0.000 description 1
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 125000002015 acyclic group Chemical group 0.000 description 1
- 125000002947 alkylene group Chemical group 0.000 description 1
- 150000001408 amides Chemical class 0.000 description 1
- 150000008064 anhydrides Chemical class 0.000 description 1
- 125000003710 aryl alkyl group Chemical group 0.000 description 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 230000006835 compression Effects 0.000 description 1
- 238000007906 compression Methods 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 235000019628 coolness Nutrition 0.000 description 1
- 125000004122 cyclic group Chemical group 0.000 description 1
- 125000000753 cycloalkyl group Chemical group 0.000 description 1
- 150000001991 dicarboxylic acids Chemical class 0.000 description 1
- KORSJDCBLAPZEQ-UHFFFAOYSA-N dicyclohexylmethane-4,4'-diisocyanate Chemical compound C1CC(N=C=O)CCC1CC1CCC(N=C=O)CC1 KORSJDCBLAPZEQ-UHFFFAOYSA-N 0.000 description 1
- 238000007599 discharging Methods 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 238000012407 engineering method Methods 0.000 description 1
- 125000000524 functional group Chemical group 0.000 description 1
- 150000002334 glycols Chemical class 0.000 description 1
- 239000008187 granular material Substances 0.000 description 1
- 125000000623 heterocyclic group Chemical group 0.000 description 1
- 229930195733 hydrocarbon Natural products 0.000 description 1
- 230000000977 initiatory effect Effects 0.000 description 1
- NIMLQBUJDJZYEJ-UHFFFAOYSA-N isophorone diisocyanate Chemical compound CC1(C)CC(N=C=O)CC(C)(CN=C=O)C1 NIMLQBUJDJZYEJ-UHFFFAOYSA-N 0.000 description 1
- 230000014759 maintenance of location Effects 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 238000000034 method Methods 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 238000000465 moulding Methods 0.000 description 1
- SLCVBVWXLSEKPL-UHFFFAOYSA-N neopentyl glycol Chemical compound OCC(C)(C)CO SLCVBVWXLSEKPL-UHFFFAOYSA-N 0.000 description 1
- BDJRBEYXGGNYIS-UHFFFAOYSA-N nonanedioic acid Chemical compound OC(=O)CCCCCCCC(O)=O BDJRBEYXGGNYIS-UHFFFAOYSA-N 0.000 description 1
- OEIJHBUUFURJLI-UHFFFAOYSA-N octane-1,8-diol Chemical compound OCCCCCCCCO OEIJHBUUFURJLI-UHFFFAOYSA-N 0.000 description 1
- 239000001301 oxygen Chemical group 0.000 description 1
- 229920006149 polyester-amide block copolymer Polymers 0.000 description 1
- 229920000570 polyether Polymers 0.000 description 1
- 238000012545 processing Methods 0.000 description 1
- 230000036647 reaction Effects 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- 239000000758 substrate Substances 0.000 description 1
- 150000003457 sulfones Chemical group 0.000 description 1
- 150000003462 sulfoxides Chemical group 0.000 description 1
- 229910052717 sulfur Inorganic materials 0.000 description 1
- 239000011593 sulfur Chemical group 0.000 description 1
- 238000012360 testing method Methods 0.000 description 1
- 229920001169 thermoplastic Polymers 0.000 description 1
- 239000004416 thermosoftening plastic Substances 0.000 description 1
- 238000012546 transfer Methods 0.000 description 1
- PAPBSGBWRJIAAV-UHFFFAOYSA-N ε-Caprolactone Chemical compound O=C1CCCCCO1 PAPBSGBWRJIAAV-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
- C08G18/65—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
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)
- Polyesters Or Polycarbonates (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US716,195 | 1976-08-20 | ||
| US05/716,195 US4051111A (en) | 1976-08-20 | 1976-08-20 | Injection moldable polyurethanes |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA1114991A true CA1114991A (en) | 1981-12-22 |
Family
ID=24877128
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA285,078A Expired CA1114991A (en) | 1976-08-20 | 1977-08-19 | Injection moldable polyurethanes |
Country Status (9)
| Country | Link |
|---|---|
| US (1) | US4051111A (enExample) |
| JP (1) | JPS5325697A (enExample) |
| BE (1) | BE857966A (enExample) |
| CA (1) | CA1114991A (enExample) |
| DE (1) | DE2736681A1 (enExample) |
| FR (1) | FR2362174A1 (enExample) |
| GB (1) | GB1572629A (enExample) |
| IT (1) | IT1085373B (enExample) |
| NL (1) | NL7709012A (enExample) |
Families Citing this family (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4203875A (en) * | 1975-07-28 | 1980-05-20 | Grow Chemical Corp. | High solids urethanes and application thereof |
| US4174436A (en) * | 1975-12-31 | 1979-11-13 | Naturin-Werk Becker & Co. | Polyurethanes and food casings made therefrom |
| US4124572A (en) * | 1977-07-05 | 1978-11-07 | Uniroyal, Inc. | Thermoplastic polyurethane elastomer |
| US4551518A (en) * | 1983-07-21 | 1985-11-05 | Kuraray Co., Ltd. | Process for production of polyurethane |
| DE3502379A1 (de) * | 1985-01-25 | 1986-07-31 | Bayer Ag, 5090 Leverkusen | Endstaendige hydroxylgruppen aufweisende polyesterpolyurethane und ihre verwendung als klebstoffe oder zur herstellung von klebstoffen |
| US6521164B1 (en) | 1996-02-06 | 2003-02-18 | Parker-Hannifin Corporation | Injection-moldable thermoplastic polyurethane elastomer |
| GB9809257D0 (en) | 1998-04-30 | 1998-07-01 | Zeneca Ltd | Polyurethane dispersants |
Family Cites Families (11)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2953539A (en) * | 1957-11-04 | 1960-09-20 | Gen Tire & Rubber Co | Composition comprising a rubbery reaction product of an organic polyisocyanate and adihydroxy terminated polyester |
| DE1114318B (de) * | 1960-05-31 | 1961-09-28 | Bayer Ag | Verfahren zur Herstellung von vernetzten homogenen Elastomeren |
| US3196026A (en) * | 1961-05-09 | 1965-07-20 | Timesaver Products Company | Process for the production of nonfoamed, urethane-type polymers |
| DE1157772B (de) * | 1962-06-01 | 1963-11-21 | Bayer Ag | Verfahren zur Herstellung von thermoplastisch verformbaren Kunststoffen |
| GB1040365A (en) * | 1964-02-20 | 1966-08-24 | British Nylon Spinners Ltd | Improvements in or relating to the manufacture of synthetic polyurethane elastomers |
| DE1301567B (de) * | 1965-05-08 | 1969-08-21 | Ealstomer Ag | Verfahren zur Herstellung von vernetzten, Urethangruppen aufweisenden, elastomeren Formkoerpern |
| US3523101A (en) * | 1965-05-15 | 1970-08-04 | Elastomer Ag | Thermoplastic polycaprolactone polyurethanes |
| US3658756A (en) * | 1969-06-05 | 1972-04-25 | Elastomer Ag | Thermoplastic polyurethanes prepared from caprolactone polyesters and method of preparation |
| US3620905A (en) * | 1969-10-21 | 1971-11-16 | Du Pont | Optically clear thermoplastic polyurethanes |
| US3931113A (en) * | 1971-06-21 | 1976-01-06 | Ppg Industries, Inc. | Impact-resistant thermoplastic polyester urethanes |
| US3900446A (en) * | 1972-12-08 | 1975-08-19 | Monsanto Co | Polyurethane interlayer for laminated safety glass |
-
1976
- 1976-08-20 US US05/716,195 patent/US4051111A/en not_active Expired - Lifetime
-
1977
- 1977-08-16 DE DE19772736681 patent/DE2736681A1/de not_active Withdrawn
- 1977-08-16 NL NL7709012A patent/NL7709012A/xx not_active Application Discontinuation
- 1977-08-19 BE BE180315A patent/BE857966A/xx not_active IP Right Cessation
- 1977-08-19 FR FR7725473A patent/FR2362174A1/fr active Granted
- 1977-08-19 IT IT26830/77A patent/IT1085373B/it active
- 1977-08-19 GB GB34826/77A patent/GB1572629A/en not_active Expired
- 1977-08-19 CA CA285,078A patent/CA1114991A/en not_active Expired
- 1977-08-20 JP JP9911477A patent/JPS5325697A/ja active Pending
Also Published As
| Publication number | Publication date |
|---|---|
| IT1085373B (it) | 1985-05-28 |
| DE2736681A1 (de) | 1978-02-23 |
| JPS5325697A (en) | 1978-03-09 |
| GB1572629A (en) | 1980-07-30 |
| FR2362174B1 (enExample) | 1983-05-06 |
| BE857966A (fr) | 1977-12-16 |
| US4051111A (en) | 1977-09-27 |
| FR2362174A1 (fr) | 1978-03-17 |
| NL7709012A (nl) | 1978-02-22 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| MKEX | Expiry |