CA1287943C - Compositions de polyuree pour enduits - Google Patents

Compositions de polyuree pour enduits

Info

Publication number: CA1287943C
Authority: CA; Canada
Prior art keywords: diisocyanate; polyurea; diamine; biuret; alkyl group
Prior art date: 1986-04-25
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 - Fee Related

Application number

CA 533639

Other languages

English (en)

Inventor

Ray V. Scott, Jr.

David W. House

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.)

Honeywell UOP LLC

Original Assignee

UOP LLC

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.)

1986-04-25

Filing date

1987-04-01

Publication date

1991-08-20

1986-04-25 Priority claimed from US06/855,991 external-priority patent/US4663201A/en

1987-04-01 Application filed by UOP LLC filed Critical UOP LLC

1987-04-01 Priority to CA 533639 priority Critical patent/CA1287943C/fr

1991-08-20 Application granted granted Critical

1991-08-20 Publication of CA1287943C publication Critical patent/CA1287943C/fr

Status Expired - Fee Related legal-status Critical Current

Links

229920002396 Polyurea Polymers 0.000 title claims abstract description 51
238000000576 coating method Methods 0.000 title claims abstract description 25
239000000203 mixture Substances 0.000 title abstract description 15
150000004985 diamines Chemical class 0.000 claims abstract description 24
239000005056 polyisocyanate Substances 0.000 claims abstract description 17
229920001228 polyisocyanate Polymers 0.000 claims abstract description 16
239000002184 metal Substances 0.000 claims abstract description 6
229910052751 metal Inorganic materials 0.000 claims abstract description 6
229920003023 plastic Polymers 0.000 claims abstract description 5
239000004033 plastic Substances 0.000 claims abstract description 5
239000011521 glass Substances 0.000 claims abstract description 4
239000002023 wood Substances 0.000 claims abstract description 4
125000000217 alkyl group Chemical group 0.000 claims description 29
238000000034 method Methods 0.000 claims description 29
-1 polymethylene chain Polymers 0.000 claims description 26
OHJMTUPIZMNBFR-UHFFFAOYSA-N biuret Chemical compound NC(=O)NC(N)=O OHJMTUPIZMNBFR-UHFFFAOYSA-N 0.000 claims description 22
125000005442 diisocyanate group Chemical group 0.000 claims description 21
239000002904 solvent Substances 0.000 claims description 13
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims description 12
125000004432 carbon atom Chemical group C* 0.000 claims description 12
239000011248 coating agent Substances 0.000 claims description 9
239000008096 xylene Substances 0.000 claims description 9
CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 claims description 6
238000006243 chemical reaction Methods 0.000 claims description 6
125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims description 5
IQPQWNKOIGAROB-UHFFFAOYSA-N isocyanate group Chemical group [N-]=C=O IQPQWNKOIGAROB-UHFFFAOYSA-N 0.000 claims description 5
150000004984 aromatic diamines Chemical group 0.000 claims description 4
NIMLQBUJDJZYEJ-UHFFFAOYSA-N isophorone diisocyanate Chemical compound CC1(C)CC(N=C=O)CC(C)(CN=C=O)C1 NIMLQBUJDJZYEJ-UHFFFAOYSA-N 0.000 claims description 4
YZZTZUHVGICSCS-UHFFFAOYSA-N n-butan-2-yl-4-[[4-(butan-2-ylamino)phenyl]methyl]aniline Chemical group C1=CC(NC(C)CC)=CC=C1CC1=CC=C(NC(C)CC)C=C1 YZZTZUHVGICSCS-UHFFFAOYSA-N 0.000 claims description 4
229920005862 polyol Polymers 0.000 claims description 4
150000003077 polyols Chemical class 0.000 claims description 4
125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 4
239000005058 Isophorone diisocyanate Substances 0.000 claims description 3
125000003710 aryl alkyl group Chemical group 0.000 claims description 2
239000006185 dispersion Substances 0.000 claims description 2
239000002243 precursor Substances 0.000 claims 9
UFWIBTONFRDIAS-UHFFFAOYSA-N Naphthalene Chemical compound C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 claims 6
125000004836 hexamethylene group Chemical group [H]C([H])([*:2])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[*:1] 0.000 claims 3
125000000843 phenylene group Chemical group C1(=C(C=CC=C1)*)* 0.000 claims 3
PAUHLEIGHAUFAK-UHFFFAOYSA-N 1-isocyanato-1-[(1-isocyanatocyclohexyl)methyl]cyclohexane Chemical compound C1CCCCC1(N=C=O)CC1(N=C=O)CCCCC1 PAUHLEIGHAUFAK-UHFFFAOYSA-N 0.000 claims 2
YUDRVAHLXDBKSR-UHFFFAOYSA-N [CH]1CCCCC1 Chemical compound [CH]1CCCCC1 YUDRVAHLXDBKSR-UHFFFAOYSA-N 0.000 claims 2
HJOVHMDZYOCNQW-UHFFFAOYSA-N isophorone Chemical compound CC1=CC(=O)CC(C)(C)C1 HJOVHMDZYOCNQW-UHFFFAOYSA-N 0.000 claims 2
238000001704 evaporation Methods 0.000 claims 1
150000003254 radicals Chemical class 0.000 claims 1
YBRVSVVVWCFQMG-UHFFFAOYSA-N 4,4'-diaminodiphenylmethane Chemical compound C1=CC(N)=CC=C1CC1=CC=C(N)C=C1 YBRVSVVVWCFQMG-UHFFFAOYSA-N 0.000 abstract description 2
239000012948 isocyanate Substances 0.000 abstract description 2
150000002513 isocyanates Chemical class 0.000 abstract description 2
239000003795 chemical substances by application Substances 0.000 description 10
JOYRKODLDBILNP-UHFFFAOYSA-N Ethyl urethane Chemical compound CCOC(N)=O JOYRKODLDBILNP-UHFFFAOYSA-N 0.000 description 9
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 9
239000000463 material Substances 0.000 description 7
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 6
229920000642 polymer Polymers 0.000 description 6
239000000047 product Substances 0.000 description 6
ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 5
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 5
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 5
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 4
241001112258 Moca Species 0.000 description 4
239000000853 adhesive Substances 0.000 description 4
230000001070 adhesive effect Effects 0.000 description 4
239000004814 polyurethane Substances 0.000 description 4
239000000126 substance Substances 0.000 description 4
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
239000004970 Chain extender Substances 0.000 description 3
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
238000005299 abrasion Methods 0.000 description 3
230000008901 benefit Effects 0.000 description 3
229920001971 elastomer Polymers 0.000 description 3
239000000806 elastomer Substances 0.000 description 3
RRAMGCGOFNQTLD-UHFFFAOYSA-N hexamethylene diisocyanate Chemical compound O=C=NCCCCCCN=C=O RRAMGCGOFNQTLD-UHFFFAOYSA-N 0.000 description 3
229920002635 polyurethane Polymers 0.000 description 3
239000007787 solid Substances 0.000 description 3
QKOWXXDOHMJOMQ-UHFFFAOYSA-N 1,3,5-tris(6-isocyanatohexyl)biuret Chemical compound O=C=NCCCCCCNC(=O)N(CCCCCCN=C=O)C(=O)NCCCCCCN=C=O QKOWXXDOHMJOMQ-UHFFFAOYSA-N 0.000 description 2
229940008841 1,6-hexamethylene diisocyanate Drugs 0.000 description 2
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
241000288921 Desmodus Species 0.000 description 2
YNQLUTRBYVCPMQ-UHFFFAOYSA-N Ethylbenzene Chemical compound CCC1=CC=CC=C1 YNQLUTRBYVCPMQ-UHFFFAOYSA-N 0.000 description 2
XSTXAVWGXDQKEL-UHFFFAOYSA-N Trichloroethylene Chemical compound ClC=C(Cl)Cl XSTXAVWGXDQKEL-UHFFFAOYSA-N 0.000 description 2
125000002947 alkylene group Chemical group 0.000 description 2
150000001412 amines Chemical class 0.000 description 2
125000003277 amino group Chemical group 0.000 description 2
238000004132 cross linking Methods 0.000 description 2
125000004435 hydrogen atom Chemical group [H]* 0.000 description 2
229920001225 polyester resin Polymers 0.000 description 2
239000004645 polyester resin Substances 0.000 description 2
ODLMAHJVESYWTB-UHFFFAOYSA-N propylbenzene Chemical compound CCCC1=CC=CC=C1 ODLMAHJVESYWTB-UHFFFAOYSA-N 0.000 description 2
229920005989 resin Polymers 0.000 description 2
239000011347 resin Substances 0.000 description 2
150000003335 secondary amines Chemical class 0.000 description 2
150000005846 sugar alcohols Polymers 0.000 description 2
VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 2
MTZUIIAIAKMWLI-UHFFFAOYSA-N 1,2-diisocyanatobenzene Chemical compound O=C=NC1=CC=CC=C1N=C=O MTZUIIAIAKMWLI-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
QGLRLXLDMZCFBP-UHFFFAOYSA-N 1,6-diisocyanato-2,4,4-trimethylhexane Chemical compound O=C=NCC(C)CC(C)(C)CCN=C=O QGLRLXLDMZCFBP-UHFFFAOYSA-N 0.000 description 1
HAAITRDZHUANGT-UHFFFAOYSA-N 1-[2-[(7-chloro-1-benzothiophen-3-yl)methoxy]-2-(2,4-dichlorophenyl)ethyl]imidazole;nitric acid Chemical compound O[N+]([O-])=O.ClC1=CC(Cl)=CC=C1C(OCC=1C2=CC=CC(Cl)=C2SC=1)CN1C=NC=C1 HAAITRDZHUANGT-UHFFFAOYSA-N 0.000 description 1
SVONRAPFKPVNKG-UHFFFAOYSA-N 2-ethoxyethyl acetate Chemical compound CCOCCOC(C)=O SVONRAPFKPVNKG-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
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 1
239000004971 Cross linker Substances 0.000 description 1
239000005057 Hexamethylene diisocyanate Substances 0.000 description 1
241001236644 Lavinia Species 0.000 description 1
CBENFWSGALASAD-UHFFFAOYSA-N Ozone Chemical compound [O-][O+]=O CBENFWSGALASAD-UHFFFAOYSA-N 0.000 description 1
229910052782 aluminium Inorganic materials 0.000 description 1
XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 1
125000003118 aryl group Chemical group 0.000 description 1
150000001555 benzenes Chemical class 0.000 description 1
239000004305 biphenyl Substances 0.000 description 1
125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
230000015556 catabolic process Effects 0.000 description 1
125000006849 chlorophenylene group Chemical group 0.000 description 1
150000001875 compounds Chemical class 0.000 description 1
239000007859 condensation product Substances 0.000 description 1
238000005260 corrosion Methods 0.000 description 1
230000007797 corrosion Effects 0.000 description 1
125000004122 cyclic group Chemical group 0.000 description 1
230000003247 decreasing effect Effects 0.000 description 1
238000006731 degradation reaction Methods 0.000 description 1
AYOHIQLKSOJJQH-UHFFFAOYSA-N dibutyltin Chemical compound CCCC[Sn]CCCC AYOHIQLKSOJJQH-UHFFFAOYSA-N 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
150000002009 diols Chemical class 0.000 description 1
238000009472 formulation Methods 0.000 description 1
238000010438 heat treatment Methods 0.000 description 1
229910052739 hydrogen Inorganic materials 0.000 description 1
239000001257 hydrogen Substances 0.000 description 1
125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
150000002576 ketones Chemical class 0.000 description 1
230000014759 maintenance of location Effects 0.000 description 1
238000004519 manufacturing process Methods 0.000 description 1
150000002739 metals Chemical class 0.000 description 1
229920003225 polyurethane elastomer Polymers 0.000 description 1
229920003226 polyurethane urea 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
230000009257 reactivity Effects 0.000 description 1
229920006395 saturated elastomer Polymers 0.000 description 1
239000000565 sealant Substances 0.000 description 1
239000000725 suspension Substances 0.000 description 1
229920001169 thermoplastic Polymers 0.000 description 1
229920001187 thermosetting polymer Polymers 0.000 description 1
239000004416 thermosoftening plastic Substances 0.000 description 1
UBOXGVDOUJQMTN-UHFFFAOYSA-N trichloroethylene Natural products ClCC(Cl)Cl UBOXGVDOUJQMTN-UHFFFAOYSA-N 0.000 description 1
150000003673 urethanes Chemical class 0.000 description 1
150000003738 xylenes Chemical class 0.000 description 1

Landscapes

Polyurethanes Or Polyureas (AREA)

CA 533639 1986-04-25 1987-04-01 Compositions de polyuree pour enduits Expired - Fee Related CA1287943C (fr)

Priority Applications (1)

Application Number	Priority Date	Filing Date	Title
CA 533639 CA1287943C (fr)	1986-04-25	1987-04-01	Compositions de polyuree pour enduits

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
US06/855,991 US4663201A (en)	1986-04-25	1986-04-25	Polyurea coatings for objects of metal glass wood or plastic
CA 533639 CA1287943C (fr)	1986-04-25	1987-04-01	Compositions de polyuree pour enduits

Publications (1)

Publication Number	Publication Date
CA1287943C true CA1287943C (fr)	1991-08-20

Family

ID=25671292

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CA 533639 Expired - Fee Related CA1287943C (fr)	1986-04-25	1987-04-01	Compositions de polyuree pour enduits

Country Status (1)

Country	Link
CA (1)	CA1287943C (fr)

1987
- 1987-04-01 CA CA 533639 patent/CA1287943C/fr not_active Expired - Fee Related

Legal Events

Date	Code	Title	Description
1994-02-22	MKLA	Lapsed

Publication	Publication Date	Title
US4663201A (en)	1987-05-05	Polyurea coatings for objects of metal glass wood or plastic
KR900006909B1 (ko)	1990-09-24	폴리우레탄에 기초한 화학적으로 경화시키는 2성분계 물질로 되는 조성물 및 그의 제조방법
KR0149051B1 (ko)	1998-10-15	폴리우레탄 및 폴리우레아용 경화제로서의 비스(n-알킬아미노시클로헥실)메탄
US7339020B2 (en)	2008-03-04	High-functionality polyisocyanates
CA1130495A (fr)	1982-08-24	Enduit thermocurable, et methode d'enduction de substrats
CA1248280A (fr)	1989-01-03	Agents de polymerisation utilises dans la fabrication de polyurethannes
US3770703A (en)	1973-11-06	Heat hardenable mixtures of epsilon-caprolactam blocked polyisocyanates and cycloaliphatic polyamines
CA2190574A1 (fr)	1997-06-23	Diisocyanates de diphenylmethane modifies par l'allophanate; methodes de preparation et utilisation
US4714512A (en)	1987-12-22	Polyurethane coatings and adhesives
JP2006307224A (ja)	2006-11-09	スルホネート基含有ポリイソシアネート及びポリアスパルテートを含む被覆組成物
KR20030038782A (ko)	2003-05-16	분무 폴리우레아 코팅계
US4383070A (en)	1983-05-10	Storage stable polyurethane compositions
US3049514A (en)	1962-08-14	Ordered hydroxy-terminated tertiarynitrogen-containing polyether-based urethane compositions
KR970015566A (ko)	1997-04-28	알로파네이트기 및 블록화 이소시아네이트기를 함유하는 디페닐메탄 디이소시아네이트 기재 폴리이소시아네이트
US4677179A (en)	1987-06-30	Storage stable, heat curable, coating composition
CA1155137A (fr)	1983-10-11	Diamines aromatiques et leur polymerisation en polyurethanes
US7655309B2 (en)	2010-02-02	Isocyanate-reactive component for preparing a polyurethane-polyurea polymer
CA1287943C (fr)	1991-08-20	Compositions de polyuree pour enduits
US4783517A (en)	1988-11-08	Polyureas as coatings
US4874831A (en)	1989-10-17	Room-temperature-cured polyurethanes and polyureas
JPH03192110A (ja)	1991-08-22	ブロックトイソシアネート及びその製造ならびに用途
JP2006506490A5 (fr)	2006-12-28
KR920001487B1 (ko)	1992-02-15	피복용 폴리우레아
HU205960B (en)	1992-07-28	Process for producing finegrain polyisocyanates coated with polymere
EP0285716A1 (fr)	1988-10-12	Composition de polyurée utile pour des revêtements