CA1144569A - Hydrolyse de polyurethanes en phase gazeuse - Google Patents

Hydrolyse de polyurethanes en phase gazeuse

Info

Publication number: CA1144569A
Authority: CA; Canada
Prior art keywords: accordance; basically reacting; alkali metal; foam; polyurethane
Prior art date: 1977-10-20
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

Application number

CA000310616A

Other languages

English (en)

Inventor

John L. Gerlock

Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)

Ford Motor Company of Canada Ltd

Original Assignee

Ford Motor Company of Canada Ltd

Priority date (The priority date 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 date listed.)

1977-10-20

Filing date

1978-09-05

Publication date

1983-04-12

1978-09-05 Application filed by Ford Motor Company of Canada Ltd filed Critical Ford Motor Company of Canada Ltd

1978-11-08 Priority to US05/958,909 priority Critical patent/US4182716A/en

1983-04-12 Application granted granted Critical

1983-04-12 Publication of CA1144569A publication Critical patent/CA1144569A/fr

Status Expired legal-status Critical Current

Links

238000006460 hydrolysis reaction Methods 0.000 title claims abstract description 26
230000007062 hydrolysis Effects 0.000 title claims abstract description 25
239000004814 polyurethane Substances 0.000 title claims abstract description 17
229920002635 polyurethane Polymers 0.000 title claims abstract description 16
239000012808 vapor phase Substances 0.000 title abstract 2
239000006260 foam Substances 0.000 claims abstract description 33
239000011496 polyurethane foam Substances 0.000 claims abstract description 10
229920005830 Polyurethane Foam Polymers 0.000 claims abstract description 9
229910052783 alkali metal Inorganic materials 0.000 claims abstract description 9
150000001340 alkali metals Chemical class 0.000 claims abstract description 9
150000001341 alkaline earth metal compounds Chemical class 0.000 claims abstract description 5
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 claims description 36
238000000034 method Methods 0.000 claims description 24
150000001875 compounds Chemical class 0.000 claims description 14
238000000354 decomposition reaction Methods 0.000 claims description 14
229920005862 polyol Polymers 0.000 claims description 8
150000003077 polyols Chemical class 0.000 claims description 8
239000007864 aqueous solution Substances 0.000 claims description 5
150000008044 alkali metal hydroxides Chemical class 0.000 claims description 4
150000004985 diamines Chemical class 0.000 claims description 4
239000007788 liquid Substances 0.000 claims description 4
239000007787 solid Substances 0.000 claims description 2
150000003388 sodium compounds Chemical class 0.000 claims 3
229910052784 alkaline earth metal Inorganic materials 0.000 claims 2
150000001342 alkaline earth metals Chemical class 0.000 claims 2
230000003197 catalytic effect Effects 0.000 abstract description 3
238000006243 chemical reaction Methods 0.000 description 8
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 7
QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 6
LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 5
239000004615 ingredient Substances 0.000 description 5
239000000047 product Substances 0.000 description 5
239000000243 solution Substances 0.000 description 5
150000001412 amines Chemical class 0.000 description 4
239000000463 material Substances 0.000 description 4
VOZKAJLKRJDJLL-UHFFFAOYSA-N 2,4-diaminotoluene Chemical compound CC1=CC=C(N)C=C1N VOZKAJLKRJDJLL-UHFFFAOYSA-N 0.000 description 3
DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 3
KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
229910021529 ammonia Inorganic materials 0.000 description 3
239000003054 catalyst Substances 0.000 description 3
-1 dimethylaminomorpholine triethylene-d Chemical compound 0.000 description 3
238000001035 drying Methods 0.000 description 3
XLYOFNOQVPJJNP-UHFFFAOYSA-M hydroxide Chemical compound [OH-] XLYOFNOQVPJJNP-UHFFFAOYSA-M 0.000 description 3
WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 3
229910052708 sodium Inorganic materials 0.000 description 3
239000011734 sodium Substances 0.000 description 3
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
JOYRKODLDBILNP-UHFFFAOYSA-N Ethyl urethane Chemical compound CCOC(N)=O JOYRKODLDBILNP-UHFFFAOYSA-N 0.000 description 2
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
XSTXAVWGXDQKEL-UHFFFAOYSA-N Trichloroethylene Chemical compound ClC=C(Cl)Cl XSTXAVWGXDQKEL-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
150000004703 alkoxides Chemical class 0.000 description 2
238000004458 analytical method Methods 0.000 description 2
238000013459 approach Methods 0.000 description 2
WERYXYBDKMZEQL-UHFFFAOYSA-N butane-1,4-diol Chemical compound OCCCCO WERYXYBDKMZEQL-UHFFFAOYSA-N 0.000 description 2
238000005516 engineering process Methods 0.000 description 2
150000002148 esters Chemical class 0.000 description 2
238000001125 extrusion Methods 0.000 description 2
239000006261 foam material Substances 0.000 description 2
238000005187 foaming Methods 0.000 description 2
239000000203 mixture Substances 0.000 description 2
239000004094 surface-active agent Substances 0.000 description 2
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 2
IMNIMPAHZVJRPE-UHFFFAOYSA-N triethylenediamine Chemical compound C1CN2CCN1CC2 IMNIMPAHZVJRPE-UHFFFAOYSA-N 0.000 description 2
GHYOCDFICYLMRF-UTIIJYGPSA-N (2S,3R)-N-[(2S)-3-(cyclopenten-1-yl)-1-[(2R)-2-methyloxiran-2-yl]-1-oxopropan-2-yl]-3-hydroxy-3-(4-methoxyphenyl)-2-[[(2S)-2-[(2-morpholin-4-ylacetyl)amino]propanoyl]amino]propanamide Chemical compound C1(=CCCC1)C[C@@H](C(=O)[C@@]1(OC1)C)NC([C@H]([C@@H](C1=CC=C(C=C1)OC)O)NC([C@H](C)NC(CN1CCOCC1)=O)=O)=O GHYOCDFICYLMRF-UTIIJYGPSA-N 0.000 description 1
HMUNWXXNJPVALC-UHFFFAOYSA-N 1-[4-[2-(2,3-dihydro-1H-inden-2-ylamino)pyrimidin-5-yl]piperazin-1-yl]-2-(2,4,6,7-tetrahydrotriazolo[4,5-c]pyridin-5-yl)ethanone Chemical compound C1C(CC2=CC=CC=C12)NC1=NC=C(C=N1)N1CCN(CC1)C(CN1CC2=C(CC1)NN=N2)=O HMUNWXXNJPVALC-UHFFFAOYSA-N 0.000 description 1
VZSRBBMJRBPUNF-UHFFFAOYSA-N 2-(2,3-dihydro-1H-inden-2-ylamino)-N-[3-oxo-3-(2,4,6,7-tetrahydrotriazolo[4,5-c]pyridin-5-yl)propyl]pyrimidine-5-carboxamide Chemical compound C1C(CC2=CC=CC=C12)NC1=NC=C(C=N1)C(=O)NCCC(N1CC2=C(CC1)NN=N2)=O VZSRBBMJRBPUNF-UHFFFAOYSA-N 0.000 description 1
TVTJUIAKQFIXCE-HUKYDQBMSA-N 2-amino-9-[(2R,3S,4S,5R)-4-fluoro-3-hydroxy-5-(hydroxymethyl)oxolan-2-yl]-7-prop-2-ynyl-1H-purine-6,8-dione Chemical compound NC=1NC(C=2N(C(N(C=2N=1)[C@@H]1O[C@@H]([C@H]([C@H]1O)F)CO)=O)CC#C)=O TVTJUIAKQFIXCE-HUKYDQBMSA-N 0.000 description 1
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 1
OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 1
239000004721 Polyphenylene oxide Substances 0.000 description 1
XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical compound [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 description 1
XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-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
238000010521 absorption reaction Methods 0.000 description 1
239000001361 adipic acid Substances 0.000 description 1
235000011037 adipic acid Nutrition 0.000 description 1
150000001408 amides Chemical class 0.000 description 1
229910052791 calcium Inorganic materials 0.000 description 1
239000011575 calcium Substances 0.000 description 1
238000011088 calibration curve Methods 0.000 description 1
239000004202 carbamide Substances 0.000 description 1
239000007795 chemical reaction product Substances 0.000 description 1
229940125797 compound 12 Drugs 0.000 description 1
229940125851 compound 27 Drugs 0.000 description 1
229920001577 copolymer Polymers 0.000 description 1
239000006071 cream Substances 0.000 description 1
239000012975 dibutyltin dilaurate Substances 0.000 description 1
ZBCBWPMODOFKDW-UHFFFAOYSA-N diethanolamine Chemical compound OCCNCCO ZBCBWPMODOFKDW-UHFFFAOYSA-N 0.000 description 1
125000005442 diisocyanate group Chemical group 0.000 description 1
239000003085 diluting agent Substances 0.000 description 1
229910001873 dinitrogen Inorganic materials 0.000 description 1
238000007598 dipping method Methods 0.000 description 1
230000000694 effects Effects 0.000 description 1
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
238000001704 evaporation Methods 0.000 description 1
230000008020 evaporation Effects 0.000 description 1
239000000945 filler Substances 0.000 description 1
238000013012 foaming technology Methods 0.000 description 1
238000009472 formulation Methods 0.000 description 1
238000010438 heat treatment Methods 0.000 description 1
239000001257 hydrogen Substances 0.000 description 1
229910052739 hydrogen Inorganic materials 0.000 description 1
230000003301 hydrolyzing effect Effects 0.000 description 1
238000007654 immersion Methods 0.000 description 1
239000011261 inert gas Substances 0.000 description 1
238000002347 injection Methods 0.000 description 1
239000007924 injection Substances 0.000 description 1
230000031700 light absorption Effects 0.000 description 1
238000004519 manufacturing process Methods 0.000 description 1
150000002736 metal compounds Chemical class 0.000 description 1
238000002156 mixing Methods 0.000 description 1
239000003960 organic solvent Substances 0.000 description 1
239000000049 pigment Substances 0.000 description 1
229920000728 polyester Polymers 0.000 description 1
229920000570 polyether Polymers 0.000 description 1
229920001228 polyisocyanate Polymers 0.000 description 1
239000005056 polyisocyanate Substances 0.000 description 1
RPDAUEIUDPHABB-UHFFFAOYSA-N potassium ethoxide Chemical compound [K+].CC[O-] RPDAUEIUDPHABB-UHFFFAOYSA-N 0.000 description 1
238000011084 recovery Methods 0.000 description 1
229910052710 silicon Inorganic materials 0.000 description 1
239000010703 silicon Substances 0.000 description 1
238000005507 spraying Methods 0.000 description 1
239000010902 straw Substances 0.000 description 1
239000000126 substance Substances 0.000 description 1
238000004448 titration Methods 0.000 description 1

Classifications

- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02W—CLIMATE CHANGE MITIGATION TECHNOLOGIES RELATED TO WASTEWATER TREATMENT OR WASTE MANAGEMENT
- Y02W30/00—Technologies for solid waste management
- Y02W30/50—Reuse, recycling or recovery technologies
- Y02W30/62—Plastics recycling; Rubber recycling

Landscapes

Polyurethanes Or Polyureas (AREA)
Separation, Recovery Or Treatment Of Waste Materials Containing Plastics (AREA)
Manufacture Of Porous Articles, And Recovery And Treatment Of Waste Products (AREA)

CA000310616A 1977-10-20 1978-09-05 Hydrolyse de polyurethanes en phase gazeuse Expired CA1144569A (fr)

Priority Applications (1)

Application Number	Priority Date	Filing Date	Title
US05/958,909 US4182716A (en)	1978-09-05	1978-11-08	Method of making 5,6-dihydro-2-methyl-N-phenyl-1,4-oxathiin-3-carboxamide

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
US84377777A	1977-10-20	1977-10-20
US843,777		1992-02-19

Publications (1)

Publication Number	Publication Date
CA1144569A true CA1144569A (fr)	1983-04-12

Family

ID=25290985

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CA000310616A Expired CA1144569A (fr)	1977-10-20	1978-09-05	Hydrolyse de polyurethanes en phase gazeuse

Country Status (2)

Country	Link
JP (1)	JPS5470377A (fr)
CA (1)	CA1144569A (fr)

Cited By (3)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US4511680A (en) *	1982-09-01	1985-04-16	Bayer Aktiengesellschaft	Process for the continuous high temperature glycolytic cleavage of polyurethane plastics waste in screw machines
US6489373B2 (en)	1998-10-02	2002-12-03	Mitsui Takeda Chemicals Inc.	Method for decomposition and recovery of polyurethane resin
US12612503B2 (en) *	2020-08-24	2026-04-28	Evonik Operations Gmbh	Depolymerization method for polyurethanes

Families Citing this family (3)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US5476624A (en) *	1991-07-05	1995-12-19	Kabushiki Kaisha Toyota Chuo Kenkyusho	Process for reclaiming waste plastics having a paint film
DE69828498T2 (de) *	1997-02-05	2006-01-19	Kabushiki Kaisha Kobe Seiko Sho, Kobe	Apparat und verfahren zum hydrolysieren und zum recycling von isocyanatverbindungen
JP4574278B2 (ja) *	2004-08-09	2010-11-04	株式会社イノアックコーポレーション	軟質ポリウレタンフォームの製造方法

1978
- 1978-09-05 CA CA000310616A patent/CA1144569A/fr not_active Expired
- 1978-10-20 JP JP12868278A patent/JPS5470377A/ja active Pending

Cited By (3)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US4511680A (en) *	1982-09-01	1985-04-16	Bayer Aktiengesellschaft	Process for the continuous high temperature glycolytic cleavage of polyurethane plastics waste in screw machines
US6489373B2 (en)	1998-10-02	2002-12-03	Mitsui Takeda Chemicals Inc.	Method for decomposition and recovery of polyurethane resin
US12612503B2 (en) *	2020-08-24	2026-04-28	Evonik Operations Gmbh	Depolymerization method for polyurethanes

Also Published As

Publication number	Publication date
JPS5470377A (en)	1979-06-06

Legal Events

Date	Code	Title	Description
2000-04-12	MKEX	Expiry

Publication	Publication Date	Title
US12612503B2 (en)	2026-04-28	Depolymerization method for polyurethanes
US3215652A (en)	1965-11-02	Process for producing a rigid polyether-polyurethane foam
Nicholas et al.	1965	Heat resistant rigid foams by trimerization of isocyanate terminated prepolymers
EP0114970B1 (fr)	1990-12-05	Procédé pour la préparation de polyméthylène-polyphényl-polyisocyanates
JP7678087B2 (ja)	2025-05-15	温和な条件下でのポリウレタンの解重合
SU795491A3 (ru)	1981-01-07	Способ получени пенополиизоцианура-TA
CA1225999A (fr)	1987-08-25	Preparation en plusieurs etapes d'hexamethylene- diisocyanate-1,6 et (ou) de diisocyanates aliphatiques isomeres avec un radial alcoylene de six atomes de carbone
Simons et al.	1960	The polymerization of propylene oxide
US4162995A (en)	1979-07-31	Method and composition for reclaiming polyurethane
US4247654A (en)	1981-01-27	Alkoxylated formose polyols and their use in polyurethane plastics
EP0011662B1 (fr)	1983-09-14	Hydrolyse de polyuréthannes
EP0629193A1 (fr)	1994-12-21	Preparation de trimeres d'osocyanate a l'aide de catalyseurs polymeres lies
KR100463976B1 (ko)	2005-09-26	이소시아네이트기및이소시아네이트기에대한반응성이차단된기의화합물
WO1991014725A1 (fr)	1991-10-03	Procede de production de polyurethane
JPH051014A (ja)	1993-01-08	トルエンジイソシアネート中の加水分解性塩化物の減少方法
JPS6360021B2 (fr)	1988-11-22
US5169878A (en)	1992-12-08	Composition and method of preparation of viscosity-stabilized polyisocyanates comprising triazine groups
US7705106B2 (en)	2010-04-27	Initial compounds for producing polyurethanes
RU2004534C1 (ru)	1993-12-15	Способ получени 2-бромперфторэтилгипофторита
Coutinho et al.	1988	Kinetic study of the reaction between a hydroxylated polybutadiene and isocyanates in chlorobenzene, III. Reaction with dimer diacid diisocyanate (DDI)
JPS5923302B2 (ja)	1984-06-01	フルオロアルキル基含有脂環式ウレタン化合物の製造方法
US3629325A (en)	1971-12-21	Cleaving poly(alkylene oxides) with acid anhydrides
Quérat et al.	1994	Hydroxamic acid esters and oximes as isocyanate blocking agents. Study on thermal dissociation
JP2006188431A (ja)	2006-07-20	含フッ素ウレタン化合物およびその用途
EP0054294B1 (fr)	1985-10-16	Procédé de transformation de groupes isocyanato en groupes carbodiimido et/ou uréthonimino

CA1144569A - Hydrolyse de polyurethanes en phase gazeuse - Google Patents

Info

Links

Classifications

Landscapes

Priority Applications (1)

Applications Claiming Priority (2)

Publications (1)

Family

ID=25290985

Family Applications (1)

Country Status (2)

Cited By (3)

Families Citing this family (3)

Cited By (3)

Also Published As

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Legal Events