CA1062393A - Revetements de polyurethane composites - Google Patents

Revetements de polyurethane composites

Info

Publication number: CA1062393A
Authority: CA; Canada
Prior art keywords: glycidyl ether; coating composition; nco; polyol; ether
Prior art date: 1975-01-20
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

CA218,179A

Other languages

English (en)

Other versions

CA218179S (en

Inventor

Benny G. Barron

Russell H. Cramm

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.)

Dow Chemical Co

Original Assignee

Dow Chemical Co

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.)

1975-01-20

Filing date

1975-01-20

Publication date

1979-09-11

1975-01-20 Application filed by Dow Chemical Co filed Critical Dow Chemical Co

1975-01-20 Priority to CA218,179A priority Critical patent/CA1062393A/fr

1979-09-11 Application granted granted Critical

1979-09-11 Publication of CA1062393A publication Critical patent/CA1062393A/fr

Status Expired legal-status Critical Current

Links

239000011527 polyurethane coating Substances 0.000 title claims description 6
GYZLOYUZLJXAJU-UHFFFAOYSA-N diglycidyl ether Chemical compound C1OC1COCC1CO1 GYZLOYUZLJXAJU-UHFFFAOYSA-N 0.000 claims abstract description 17
229920005862 polyol Polymers 0.000 claims abstract description 15
150000003077 polyols Chemical class 0.000 claims abstract description 15
LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 claims abstract description 12
239000002904 solvent Substances 0.000 claims abstract description 12
PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 claims abstract description 10
229930195733 hydrocarbon Natural products 0.000 claims abstract description 10
-1 alicyclic hydrocarbon Chemical class 0.000 claims abstract description 9
239000004215 Carbon black (E152) Substances 0.000 claims abstract description 8
150000001875 compounds Chemical class 0.000 claims abstract description 8
239000007795 chemical reaction product Substances 0.000 claims abstract description 6
125000005442 diisocyanate group Chemical group 0.000 claims abstract description 6
239000003999 initiator Substances 0.000 claims abstract description 6
235000011187 glycerol Nutrition 0.000 claims abstract description 5
DURPTKYDGMDSBL-UHFFFAOYSA-N 1-butoxybutane Chemical compound CCCCOCCCC DURPTKYDGMDSBL-UHFFFAOYSA-N 0.000 claims abstract description 3
239000000203 mixture Substances 0.000 claims description 14
239000008199 coating composition Substances 0.000 claims description 8
125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 8
150000002430 hydrocarbons Chemical class 0.000 claims description 7
DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 claims description 6
239000003054 catalyst Substances 0.000 claims description 6
SZNYYWIUQFZLLT-UHFFFAOYSA-N 2-methyl-1-(2-methylpropoxy)propane Chemical compound CC(C)COCC(C)C SZNYYWIUQFZLLT-UHFFFAOYSA-N 0.000 claims description 4
125000004432 carbon atom Chemical group C* 0.000 claims description 4
ZSIAUFGUXNUGDI-UHFFFAOYSA-N hexan-1-ol Chemical compound CCCCCCO ZSIAUFGUXNUGDI-UHFFFAOYSA-N 0.000 claims description 4
239000000758 substrate Substances 0.000 claims description 4
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 2
239000001257 hydrogen Substances 0.000 claims description 2
229910052739 hydrogen Inorganic materials 0.000 claims description 2
125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 2
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 2
DVKJHBMWWAPEIU-UHFFFAOYSA-N toluene 2,4-diisocyanate Chemical group CC1=CC=C(N=C=O)C=C1N=C=O DVKJHBMWWAPEIU-UHFFFAOYSA-N 0.000 claims description 2
125000001931 aliphatic group Chemical group 0.000 abstract 1
150000002170 ethers Chemical class 0.000 abstract 1
238000000576 coating method Methods 0.000 description 9
239000011248 coating agent Substances 0.000 description 6
239000000047 product Substances 0.000 description 5
QQZOPKMRPOGIEB-UHFFFAOYSA-N 2-Oxohexane Chemical compound CCCCC(C)=O QQZOPKMRPOGIEB-UHFFFAOYSA-N 0.000 description 4
UKLDJPRMSDWDSL-UHFFFAOYSA-L [dibutyl(dodecanoyloxy)stannyl] dodecanoate Chemical compound CCCCCCCCCCCC(=O)O[Sn](CCCC)(CCCC)OC(=O)CCCCCCCCCCC UKLDJPRMSDWDSL-UHFFFAOYSA-L 0.000 description 4
239000012975 dibutyltin dilaurate Substances 0.000 description 4
238000002360 preparation method Methods 0.000 description 4
MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 3
AFABGHUZZDYHJO-UHFFFAOYSA-N dimethyl butane Natural products CCCC(C)C AFABGHUZZDYHJO-UHFFFAOYSA-N 0.000 description 3
RUELTTOHQODFPA-UHFFFAOYSA-N toluene 2,6-diisocyanate Chemical compound CC1=C(N=C=O)C=CC=C1N=C=O RUELTTOHQODFPA-UHFFFAOYSA-N 0.000 description 3
229910015900 BF3 Inorganic materials 0.000 description 2
KZMGYPLQYOPHEL-UHFFFAOYSA-N Boron trifluoride etherate Chemical compound FB(F)F.CCOCC KZMGYPLQYOPHEL-UHFFFAOYSA-N 0.000 description 2
RGSFGYAAUTVSQA-UHFFFAOYSA-N Cyclopentane Chemical compound C1CCCC1 RGSFGYAAUTVSQA-UHFFFAOYSA-N 0.000 description 2
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
238000009835 boiling Methods 0.000 description 2
DIOQZVSQGTUSAI-UHFFFAOYSA-N decane Chemical compound CCCCCCCCCC DIOQZVSQGTUSAI-UHFFFAOYSA-N 0.000 description 2
239000012948 isocyanate Substances 0.000 description 2
QWTDNUCVQCZILF-UHFFFAOYSA-N isopentane Chemical compound CCC(C)C QWTDNUCVQCZILF-UHFFFAOYSA-N 0.000 description 2
238000000034 method Methods 0.000 description 2
UAEPNZWRGJTJPN-UHFFFAOYSA-N methylcyclohexane Chemical compound CC1CCCCC1 UAEPNZWRGJTJPN-UHFFFAOYSA-N 0.000 description 2
IMNIMPAHZVJRPE-UHFFFAOYSA-N triethylenediamine Chemical compound C1CN2CCN1CC2 IMNIMPAHZVJRPE-UHFFFAOYSA-N 0.000 description 2
NKJOXAZJBOMXID-UHFFFAOYSA-N 1,1'-Oxybisoctane Chemical compound CCCCCCCCOCCCCCCCC NKJOXAZJBOMXID-UHFFFAOYSA-N 0.000 description 1
OVBFMUAFNIIQAL-UHFFFAOYSA-N 1,4-diisocyanatobutane Chemical compound O=C=NCCCCN=C=O OVBFMUAFNIIQAL-UHFFFAOYSA-N 0.000 description 1
JPEGUDKOYOIOOP-UHFFFAOYSA-N 2-(hexoxymethyl)oxirane Chemical compound CCCCCCOCC1CO1 JPEGUDKOYOIOOP-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
HVCNXQOWACZAFN-UHFFFAOYSA-N 4-ethylmorpholine Chemical compound CCN1CCOCC1 HVCNXQOWACZAFN-UHFFFAOYSA-N 0.000 description 1
XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 1
239000005057 Hexamethylene diisocyanate Substances 0.000 description 1
NHTMVDHEPJAVLT-UHFFFAOYSA-N Isooctane Chemical compound CC(C)CC(C)(C)C NHTMVDHEPJAVLT-UHFFFAOYSA-N 0.000 description 1
239000004721 Polyphenylene oxide Substances 0.000 description 1
GOOHAUXETOMSMM-UHFFFAOYSA-N Propylene oxide Chemical compound CC1CO1 GOOHAUXETOMSMM-UHFFFAOYSA-N 0.000 description 1
ZJCCRDAZUWHFQH-UHFFFAOYSA-N Trimethylolpropane Chemical compound CCC(CO)(CO)CO ZJCCRDAZUWHFQH-UHFFFAOYSA-N 0.000 description 1
ISKQADXMHQSTHK-UHFFFAOYSA-N [4-(aminomethyl)phenyl]methanamine Chemical compound NCC1=CC=C(CN)C=C1 ISKQADXMHQSTHK-UHFFFAOYSA-N 0.000 description 1
150000004945 aromatic hydrocarbons Chemical class 0.000 description 1
239000002585 base Substances 0.000 description 1
230000015572 biosynthetic process Effects 0.000 description 1
IISBACLAFKSPIT-UHFFFAOYSA-N bisphenol A Chemical compound C=1C=C(O)C=CC=1C(C)(C)C1=CC=C(O)C=C1 IISBACLAFKSPIT-UHFFFAOYSA-N 0.000 description 1
230000001680 brushing effect Effects 0.000 description 1
230000003197 catalytic effect Effects 0.000 description 1
238000006555 catalytic reaction Methods 0.000 description 1
150000001768 cations Chemical class 0.000 description 1
239000003795 chemical substances by application Substances 0.000 description 1
239000010960 cold rolled steel Substances 0.000 description 1
239000003086 colorant Substances 0.000 description 1
229940120693 copper naphthenate Drugs 0.000 description 1
SEVNKWFHTNVOLD-UHFFFAOYSA-L copper;3-(4-ethylcyclohexyl)propanoate;3-(3-ethylcyclopentyl)propanoate Chemical compound [Cu+2].CCC1CCC(CCC([O-])=O)C1.CCC1CCC(CCC([O-])=O)CC1 SEVNKWFHTNVOLD-UHFFFAOYSA-L 0.000 description 1
238000004132 cross linking Methods 0.000 description 1
239000008367 deionised water Substances 0.000 description 1
229910021641 deionized water Inorganic materials 0.000 description 1
238000010790 dilution Methods 0.000 description 1
239000012895 dilution Substances 0.000 description 1
JVSWJIKNEAIKJW-UHFFFAOYSA-N dimethyl-hexane Natural products CCCCCC(C)C JVSWJIKNEAIKJW-UHFFFAOYSA-N 0.000 description 1
238000001035 drying Methods 0.000 description 1
150000002148 esters Chemical class 0.000 description 1
239000004744 fabric Substances 0.000 description 1
239000003063 flame retardant Substances 0.000 description 1
238000005227 gel permeation chromatography Methods 0.000 description 1
DMEGYFMYUHOHGS-UHFFFAOYSA-N heptamethylene Natural products C1CCCCCC1 DMEGYFMYUHOHGS-UHFFFAOYSA-N 0.000 description 1
RRAMGCGOFNQTLD-UHFFFAOYSA-N hexamethylene diisocyanate Chemical compound O=C=NCCCCCCN=C=O RRAMGCGOFNQTLD-UHFFFAOYSA-N 0.000 description 1
150000002513 isocyanates Chemical class 0.000 description 1
150000002576 ketones Chemical class 0.000 description 1
GIWKOZXJDKMGQC-UHFFFAOYSA-L lead(2+);naphthalene-2-carboxylate Chemical compound [Pb+2].C1=CC=CC2=CC(C(=O)[O-])=CC=C21.C1=CC=CC2=CC(C(=O)[O-])=CC=C21 GIWKOZXJDKMGQC-UHFFFAOYSA-L 0.000 description 1
DSSXKBBEJCDMBT-UHFFFAOYSA-M lead(2+);octanoate Chemical compound [Pb+2].CCCCCCCC([O-])=O DSSXKBBEJCDMBT-UHFFFAOYSA-M 0.000 description 1
239000010985 leather Substances 0.000 description 1
239000011968 lewis acid catalyst Substances 0.000 description 1
HCWCAKKEBCNQJP-UHFFFAOYSA-N magnesium orthosilicate Chemical compound [Mg+2].[Mg+2].[O-][Si]([O-])([O-])[O-] HCWCAKKEBCNQJP-UHFFFAOYSA-N 0.000 description 1
229910052919 magnesium silicate Inorganic materials 0.000 description 1
235000019792 magnesium silicate Nutrition 0.000 description 1
239000000391 magnesium silicate Substances 0.000 description 1
239000002184 metal Substances 0.000 description 1
229910052751 metal Inorganic materials 0.000 description 1
GYNNXHKOJHMOHS-UHFFFAOYSA-N methyl-cycloheptane Natural products CC1CCCCCC1 GYNNXHKOJHMOHS-UHFFFAOYSA-N 0.000 description 1
CIXSDMKDSYXUMJ-UHFFFAOYSA-N n,n-diethylcyclohexanamine Chemical compound CCN(CC)C1CCCCC1 CIXSDMKDSYXUMJ-UHFFFAOYSA-N 0.000 description 1
125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
238000006386 neutralization reaction Methods 0.000 description 1
239000012299 nitrogen atmosphere Substances 0.000 description 1
150000002902 organometallic compounds Chemical class 0.000 description 1
WXZMFSXDPGVJKK-UHFFFAOYSA-N pentaerythritol Chemical compound OCC(CO)(CO)CO WXZMFSXDPGVJKK-UHFFFAOYSA-N 0.000 description 1
239000003209 petroleum derivative Substances 0.000 description 1
239000004033 plastic Substances 0.000 description 1
229920003023 plastic Polymers 0.000 description 1
229920000570 polyether Polymers 0.000 description 1
239000005056 polyisocyanate Substances 0.000 description 1
229920001228 polyisocyanate Polymers 0.000 description 1
230000001681 protective effect Effects 0.000 description 1
238000007761 roller coating Methods 0.000 description 1
238000005507 spraying Methods 0.000 description 1
238000003756 stirring Methods 0.000 description 1
150000003512 tertiary amines Chemical class 0.000 description 1
KSBAEPSJVUENNK-UHFFFAOYSA-L tin(ii) 2-ethylhexanoate Chemical compound [Sn+2].CCCCC(CC)C([O-])=O.CCCCC(CC)C([O-])=O KSBAEPSJVUENNK-UHFFFAOYSA-L 0.000 description 1
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
239000002023 wood Substances 0.000 description 1

Landscapes

Polyurethanes Or Polyureas (AREA)
Paints Or Removers (AREA)

CA218,179A 1975-01-20 1975-01-20 Revetements de polyurethane composites Expired CA1062393A (fr)

Priority Applications (1)

Application Number	Priority Date	Filing Date	Title
CA218,179A CA1062393A (fr)	1975-01-20	1975-01-20	Revetements de polyurethane composites

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
CA218,179A CA1062393A (fr)	1975-01-20	1975-01-20	Revetements de polyurethane composites

Publications (1)

Publication Number	Publication Date
CA1062393A true CA1062393A (fr)	1979-09-11

Family

ID=4102083

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CA218,179A Expired CA1062393A (fr)	1975-01-20	1975-01-20	Revetements de polyurethane composites

Country Status (1)

Country	Link
CA (1)	CA1062393A (fr)

1975
- 1975-01-20 CA CA218,179A patent/CA1062393A/fr not_active Expired

Legal Events

Date	Code	Title	Description
2024-03-22	MKEX	Expiry	Effective date: 19960911

Publication	Publication Date	Title
US4710560A (en)	1987-12-01	Polyurethane coating composition
CA1182945A (fr)	1985-02-19	Enduits au polyurethane, et methode de production connexe
US4788083A (en)	1988-11-29	Tin or bismuth complex catalysts and trigger cure of coatings therewith
US4798878A (en)	1989-01-17	Synthetic resin compositions shelf-stable under exclusion of moisture
AU2006299127B2 (en)	2011-12-01	Two-component systems for producing flexible coatings
KR100220788B1 (ko)	1999-10-01	휘발성 유기물 함량이 매우 낮은 폴리우레탄 피복물
US4296230A (en)	1981-10-20	Polyurethane coatings produced from (1) a polyisocyanate mixture of polyisocyanates from the diphenol methane series and a polyhydroxy polyether containing at least one tertiary amine nitrogen with (2) a polyol in a two component coating system
EP0158893A1 (fr)	1985-10-23	Prépolymères d'isocyanate contenant des silanes
US3830785A (en)	1974-08-20	Thermosetting polyurethane coatings based on blocked cyclo-aliphatic diisocyanates
JPH0211555A (ja)	1990-01-16	変性ポリイソシアネートの製造方法およびこの方法により得られるポリイソシアネートの結合剤または結合剤成分としての使用
CA1200346A (fr)	1986-02-04	Compositions de polyurethane stables en stockage
US3049513A (en)	1962-08-14	Ordered isocyanate-terminated polyether-based urethane compositions
KR970015566A (ko)	1997-04-28	알로파네이트기 및 블록화 이소시아네이트기를 함유하는 디페닐메탄 디이소시아네이트 기재 폴리이소시아네이트
CA1231499A (fr)	1988-01-12	Compositions a la resine d'urethane
MXPA01006298A (es)	2005-06-20	Composicion de recubrimiento.
AU8862298A (en)	1999-02-16	Coating agent and method for producing same
CA1062393A (fr)	1979-09-11	Revetements de polyurethane composites
CA1186442A (fr)	1985-04-30	Polyurethane mono-element durcissable
JP5132029B2 (ja)	2013-01-30	塗料組成物
US3923746A (en)	1975-12-02	One-package polyurethane coatings
KR100623320B1 (ko)	2006-09-11	충전재 조성물
US6130285A (en)	2000-10-10	Binder composition and its use for coating metallic and mineral substrates
JPS6335673B2 (fr)	1988-07-15
US6566481B2 (en)	2003-05-20	Polyisocyanates with allophanate groups derived from alicyclic alkanediols
US4611043A (en)	1986-09-09	Coating composition prepared by reacting an isocyanate prepolymer with dicyclopentenyl alcohol