JPH0330613B2 - - Google Patents
Info
- Publication number
- JPH0330613B2 JPH0330613B2 JP58072004A JP7200483A JPH0330613B2 JP H0330613 B2 JPH0330613 B2 JP H0330613B2 JP 58072004 A JP58072004 A JP 58072004A JP 7200483 A JP7200483 A JP 7200483A JP H0330613 B2 JPH0330613 B2 JP H0330613B2
- Authority
- JP
- Japan
- Prior art keywords
- hydroquinone
- glycol ether
- chain extender
- diisocyanate
- bheb
- 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 - Lifetime
Links
- QIGBRXMKCJKVMJ-UHFFFAOYSA-N Hydroquinone Chemical compound OC1=CC=C(O)C=C1 QIGBRXMKCJKVMJ-UHFFFAOYSA-N 0.000 claims description 50
- 239000004970 Chain extender Substances 0.000 claims description 24
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 claims description 18
- 239000000203 mixture Substances 0.000 claims description 16
- RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 13
- FVFPCFRANAKGKS-UHFFFAOYSA-N benzene-1,4-diol;ethane-1,2-diol Chemical compound OCCO.OC1=CC=C(O)C=C1 FVFPCFRANAKGKS-UHFFFAOYSA-N 0.000 claims description 12
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 claims description 12
- 229920005862 polyol Polymers 0.000 claims description 12
- 150000003077 polyols Chemical class 0.000 claims description 11
- 239000002202 Polyethylene glycol Substances 0.000 claims description 10
- 229920001223 polyethylene glycol Polymers 0.000 claims description 10
- 229920002635 polyurethane Polymers 0.000 claims description 10
- 239000004814 polyurethane Substances 0.000 claims description 10
- 125000005442 diisocyanate group Chemical group 0.000 claims description 8
- 239000007795 chemical reaction product Substances 0.000 claims description 6
- 239000003795 chemical substances by application Substances 0.000 claims description 6
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 6
- 239000004480 active ingredient Substances 0.000 claims description 4
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 14
- 229920001971 elastomer Polymers 0.000 description 12
- 239000000806 elastomer Substances 0.000 description 12
- 230000000704 physical effect Effects 0.000 description 12
- 230000000052 comparative effect Effects 0.000 description 11
- 238000000034 method Methods 0.000 description 11
- 239000000047 product Substances 0.000 description 10
- 239000003054 catalyst Substances 0.000 description 8
- 238000006243 chemical reaction Methods 0.000 description 7
- -1 diisocyanate compound Chemical class 0.000 description 6
- 238000002844 melting Methods 0.000 description 6
- 230000008018 melting Effects 0.000 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 description 5
- 239000012752 auxiliary agent Substances 0.000 description 5
- 150000002009 diols Chemical class 0.000 description 5
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 5
- 239000000654 additive Substances 0.000 description 4
- WERYXYBDKMZEQL-UHFFFAOYSA-N butane-1,4-diol Chemical compound OCCCCO WERYXYBDKMZEQL-UHFFFAOYSA-N 0.000 description 4
- 238000004519 manufacturing process Methods 0.000 description 4
- 229920003225 polyurethane elastomer Polymers 0.000 description 4
- 239000002904 solvent Substances 0.000 description 4
- WTPYFJNYAMXZJG-UHFFFAOYSA-N 2-[4-(2-hydroxyethoxy)phenoxy]ethanol Chemical compound OCCOC1=CC=C(OCCO)C=C1 WTPYFJNYAMXZJG-UHFFFAOYSA-N 0.000 description 3
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 229920006311 Urethane elastomer Polymers 0.000 description 3
- 150000001875 compounds Chemical class 0.000 description 3
- 238000002156 mixing Methods 0.000 description 3
- 229920000909 polytetrahydrofuran Polymers 0.000 description 3
- 238000001556 precipitation Methods 0.000 description 3
- 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 3
- IBOFVQJTBBUKMU-UHFFFAOYSA-N 4,4'-methylene-bis-(2-chloroaniline) Chemical compound C1=C(Cl)C(N)=CC=C1CC1=CC=C(N)C(Cl)=C1 IBOFVQJTBBUKMU-UHFFFAOYSA-N 0.000 description 2
- JOYRKODLDBILNP-UHFFFAOYSA-N Ethyl urethane Chemical compound CCOC(N)=O JOYRKODLDBILNP-UHFFFAOYSA-N 0.000 description 2
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 2
- 239000004721 Polyphenylene oxide Substances 0.000 description 2
- 230000000996 additive effect Effects 0.000 description 2
- 150000001412 amines Chemical class 0.000 description 2
- 238000009835 boiling Methods 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- 150000002170 ethers Chemical class 0.000 description 2
- 239000006260 foam Substances 0.000 description 2
- 150000002334 glycols Chemical class 0.000 description 2
- 239000008240 homogeneous mixture Substances 0.000 description 2
- 239000000463 material Substances 0.000 description 2
- 229920000728 polyester Polymers 0.000 description 2
- 229920000570 polyether Polymers 0.000 description 2
- 231100000419 toxicity Toxicity 0.000 description 2
- 230000001988 toxicity Effects 0.000 description 2
- PUPZLCDOIYMWBV-UHFFFAOYSA-N (+/-)-1,3-Butanediol Chemical compound CC(O)CCO PUPZLCDOIYMWBV-UHFFFAOYSA-N 0.000 description 1
- XAXULEOYEDGYGF-UHFFFAOYSA-N 2-amino-1-[2-(2-amino-1-hydroxyethyl)phenyl]ethanol Chemical compound NCC(O)C1=CC=CC=C1C(O)CN XAXULEOYEDGYGF-UHFFFAOYSA-N 0.000 description 1
- QZWKEPYTBWZJJA-UHFFFAOYSA-N 3,3'-Dimethoxybenzidine-4,4'-diisocyanate Chemical compound C1=C(N=C=O)C(OC)=CC(C=2C=C(OC)C(N=C=O)=CC=2)=C1 QZWKEPYTBWZJJA-UHFFFAOYSA-N 0.000 description 1
- 206010007269 Carcinogenicity Diseases 0.000 description 1
- 239000005057 Hexamethylene diisocyanate Substances 0.000 description 1
- 101000609947 Homo sapiens Rod cGMP-specific 3',5'-cyclic phosphodiesterase subunit alpha Proteins 0.000 description 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- CBENFWSGALASAD-UHFFFAOYSA-N Ozone Chemical compound [O-][O+]=O CBENFWSGALASAD-UHFFFAOYSA-N 0.000 description 1
- 102100039177 Rod cGMP-specific 3',5'-cyclic phosphodiesterase subunit alpha Human genes 0.000 description 1
- ZJCCRDAZUWHFQH-UHFFFAOYSA-N Trimethylolpropane Chemical compound CCC(CO)(CO)CO ZJCCRDAZUWHFQH-UHFFFAOYSA-N 0.000 description 1
- UKLDJPRMSDWDSL-UHFFFAOYSA-L [dibutyl(dodecanoyloxy)stannyl] dodecanoate Chemical compound CCCCCCCCCCCC(=O)O[Sn](CCCC)(CCCC)OC(=O)CCCCCCCCCCC UKLDJPRMSDWDSL-UHFFFAOYSA-L 0.000 description 1
- 238000005299 abrasion Methods 0.000 description 1
- 238000007259 addition reaction Methods 0.000 description 1
- 239000000853 adhesive Substances 0.000 description 1
- 230000001070 adhesive effect Effects 0.000 description 1
- 230000032683 aging Effects 0.000 description 1
- 239000012736 aqueous medium Substances 0.000 description 1
- 150000001555 benzenes Chemical class 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- 231100000260 carcinogenicity Toxicity 0.000 description 1
- 230000007670 carcinogenicity Effects 0.000 description 1
- 230000003247 decreasing effect Effects 0.000 description 1
- 230000007547 defect Effects 0.000 description 1
- 239000012975 dibutyltin dilaurate Substances 0.000 description 1
- 239000000835 fiber Substances 0.000 description 1
- 238000005187 foaming Methods 0.000 description 1
- 235000011187 glycerol Nutrition 0.000 description 1
- RRAMGCGOFNQTLD-UHFFFAOYSA-N hexamethylene diisocyanate Chemical compound O=C=NCCCCCCN=C=O RRAMGCGOFNQTLD-UHFFFAOYSA-N 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 1
- 239000012770 industrial material Substances 0.000 description 1
- 239000012948 isocyanate Substances 0.000 description 1
- IQPQWNKOIGAROB-UHFFFAOYSA-N isocyanate group Chemical group [N-]=C=O IQPQWNKOIGAROB-UHFFFAOYSA-N 0.000 description 1
- 150000002513 isocyanates Chemical class 0.000 description 1
- 231100001231 less toxic Toxicity 0.000 description 1
- 239000002075 main ingredient Substances 0.000 description 1
- 231100000252 nontoxic Toxicity 0.000 description 1
- 230000003000 nontoxic effect Effects 0.000 description 1
- WWZKQHOCKIZLMA-UHFFFAOYSA-N octanoic acid Chemical compound CCCCCCCC(O)=O WWZKQHOCKIZLMA-UHFFFAOYSA-N 0.000 description 1
- 229940049964 oleate Drugs 0.000 description 1
- ZQPPMHVWECSIRJ-KTKRTIGZSA-N oleic acid Chemical compound CCCCCCCC\C=C/CCCCCCCC(O)=O ZQPPMHVWECSIRJ-KTKRTIGZSA-N 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 238000012856 packing Methods 0.000 description 1
- 239000003973 paint Substances 0.000 description 1
- 229920001977 poly(N,N-diethylacrylamides) Polymers 0.000 description 1
- 229920005749 polyurethane resin Polymers 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 229920005989 resin Polymers 0.000 description 1
- 239000011347 resin Substances 0.000 description 1
- 239000003566 sealing material Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- ZIBGPFATKBEMQZ-UHFFFAOYSA-N triethylene glycol Chemical compound OCCOCCOCCO ZIBGPFATKBEMQZ-UHFFFAOYSA-N 0.000 description 1
- 150000004072 triols Chemical class 0.000 description 1
Landscapes
- Polyurethanes Or Polyureas (AREA)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP58072004A JPS59197417A (ja) | 1983-04-23 | 1983-04-23 | ポリウレタン用鎖延長剤 |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP58072004A JPS59197417A (ja) | 1983-04-23 | 1983-04-23 | ポリウレタン用鎖延長剤 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS59197417A JPS59197417A (ja) | 1984-11-09 |
| JPH0330613B2 true JPH0330613B2 (ko) | 1991-05-01 |
Family
ID=13476836
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP58072004A Granted JPS59197417A (ja) | 1983-04-23 | 1983-04-23 | ポリウレタン用鎖延長剤 |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPS59197417A (ko) |
Families Citing this family (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPH0791355B2 (ja) * | 1988-07-15 | 1995-10-04 | 武田薬品工業株式会社 | 硬質ウレタンフオーム用ポリオール組成物 |
| JPH0791452B2 (ja) * | 1988-11-30 | 1995-10-04 | 武田薬品工業株式会社 | 硬質ウレタンフオーム用ポリオール組成物 |
| US6521164B1 (en) | 1996-02-06 | 2003-02-18 | Parker-Hannifin Corporation | Injection-moldable thermoplastic polyurethane elastomer |
-
1983
- 1983-04-23 JP JP58072004A patent/JPS59197417A/ja active Granted
Also Published As
| Publication number | Publication date |
|---|---|
| JPS59197417A (ja) | 1984-11-09 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| EP0425694B1 (en) | Curable polyurethane composition excellent in flexibility | |
| US4242468A (en) | Use of monohydroxylated polybutadiene as a reactive plasticizer in polyurethanes | |
| US3499009A (en) | Polyols of methylenedianilines | |
| US4048104A (en) | Polyisocyanate prepolymers from scrap polyester and polyurethane foam products obtained therefrom | |
| US5496496A (en) | Process for producing polyurethane elastomers | |
| EP0617066B1 (en) | Thermosetting urethane elastomer | |
| JPH06501506A (ja) | ポリオールを使用して製造されるポリウレタンエラストマー及びポリ尿素エラストマー | |
| US4235977A (en) | Cross-linked polyurethane elastomers and microcellular foams | |
| KR100637640B1 (ko) | 폴리우레탄계/폴리우레탄우레아계 수지 및 그의 제조 방법 | |
| JPH0651776B2 (ja) | ポリエーテルのブレンドに基づくポリウレタン | |
| US4581388A (en) | Process for the production of urethane-modified polyisocyanate using an oxyalkylated bisphenol | |
| US3471445A (en) | Curable urethane compositions | |
| JPH0733423B2 (ja) | 軟質ポリウレタン発泡体の製造方法 | |
| EP1192201A1 (de) | Polyharnstoffpolyurethane mit verbesserten physikalischen eigenschaften | |
| CA2223478A1 (en) | Toluene diisocyanate residue-based compositions and the use of such compositions as fillers for hydroxyl compounds | |
| JPH0330613B2 (ko) | ||
| DE4032148A1 (de) | Verfahren zur herstellung von zelligen formkunststoffen | |
| GB2109803A (en) | High molecular weight polyether polyols | |
| EP0122894B1 (en) | Process for preparing polyurethanes with the use of a polyhydroxyalkylphosphine oxide as curative | |
| EP0235887B1 (en) | The use of polyester polyols for preparing microcellular polyurethane elastomers | |
| JP2004027054A (ja) | 新規なポリオールによるポリウレタン樹脂 | |
| US4115301A (en) | Cross-linker for flexible and semi-flexible polyurethane foams | |
| JPH05295073A (ja) | ポリウレタン系硬化性組成物 | |
| JP4495296B2 (ja) | ポリウレタンフォーム | |
| JPS58204018A (ja) | 耐熱性ポリウレタン樹脂 |