CA1282888C - Produit de reaction a base d'acrylourethane - Google Patents

Produit de reaction a base d'acrylourethane

Info

Publication number: CA1282888C
Authority: CA; Canada
Prior art keywords: reaction product; diol; diisocyanate; methacrylate; molecular weight
Prior art date: 1987-01-13
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

Application number

CA000527201A

Other languages

English (en)

Inventor

Andrew Paul Stamegna

Clifford Hugh Strolle

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.)

EIDP Inc

Original Assignee

EI Du Pont de Nemours and 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.)

1987-01-13

Filing date

1987-01-13

Publication date

1991-04-09

1987-01-13 Application filed by EI Du Pont de Nemours and Co filed Critical EI Du Pont de Nemours and Co

1987-01-13 Priority to CA000527201A priority Critical patent/CA1282888C/fr

1991-04-09 Application granted granted Critical

1991-04-09 Publication of CA1282888C publication Critical patent/CA1282888C/fr

2008-04-09 Anticipated expiration legal-status Critical

Status Expired - Lifetime legal-status Critical Current

Links

239000007795 chemical reaction product Substances 0.000 title claims abstract description 19
150000002009 diols Chemical class 0.000 claims abstract description 26
239000007787 solid Substances 0.000 claims abstract description 18
239000002253 acid Substances 0.000 claims abstract description 13
NIXOWILDQLNWCW-UHFFFAOYSA-N acrylic acid group Chemical group C(C=C)(=O)O NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 claims abstract description 12
125000005442 diisocyanate group Chemical group 0.000 claims abstract description 10
229920000642 polymer Polymers 0.000 claims abstract description 8
239000008199 coating composition Substances 0.000 claims abstract description 5
125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 12
SOGAXMICEFXMKE-UHFFFAOYSA-N Butylmethacrylate Chemical compound CCCCOC(=O)C(C)=C SOGAXMICEFXMKE-UHFFFAOYSA-N 0.000 claims description 8
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 7
239000000178 monomer Substances 0.000 claims description 7
229920005989 resin Polymers 0.000 claims description 7
239000011347 resin Substances 0.000 claims description 7
OMIGHNLMNHATMP-UHFFFAOYSA-N 2-hydroxyethyl prop-2-enoate Chemical compound OCCOC(=O)C=C OMIGHNLMNHATMP-UHFFFAOYSA-N 0.000 claims description 6
LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 claims description 6
PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 claims description 6
150000008064 anhydrides Chemical class 0.000 claims description 6
238000006243 chemical reaction Methods 0.000 claims description 5
WERYXYBDKMZEQL-UHFFFAOYSA-N butane-1,4-diol Chemical compound OCCCCO WERYXYBDKMZEQL-UHFFFAOYSA-N 0.000 claims description 4
239000004632 polycaprolactone Substances 0.000 claims description 4
GNSFRPWPOGYVLO-UHFFFAOYSA-N 3-hydroxypropyl 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OCCCO GNSFRPWPOGYVLO-UHFFFAOYSA-N 0.000 claims description 3
VVQNEPGJFQJSBK-UHFFFAOYSA-N Methyl methacrylate Chemical compound COC(=O)C(C)=C VVQNEPGJFQJSBK-UHFFFAOYSA-N 0.000 claims description 3
125000001931 aliphatic group Chemical group 0.000 claims description 3
CQEYYJKEWSMYFG-UHFFFAOYSA-N butyl acrylate Chemical compound CCCCOC(=O)C=C CQEYYJKEWSMYFG-UHFFFAOYSA-N 0.000 claims description 3
SUPCQIBBMFXVTL-UHFFFAOYSA-N ethyl 2-methylprop-2-enoate Chemical compound CCOC(=O)C(C)=C SUPCQIBBMFXVTL-UHFFFAOYSA-N 0.000 claims description 3
229920001610 polycaprolactone Polymers 0.000 claims description 3
SRPWOOOHEPICQU-UHFFFAOYSA-N trimellitic anhydride Chemical group OC(=O)C1=CC=C2C(=O)OC(=O)C2=C1 SRPWOOOHEPICQU-UHFFFAOYSA-N 0.000 claims description 3
229920002818 (Hydroxyethyl)methacrylate Polymers 0.000 claims description 2
VZXPHDGHQXLXJC-UHFFFAOYSA-N 1,6-diisocyanato-5,6-dimethylheptane Chemical compound O=C=NC(C)(C)C(C)CCCCN=C=O VZXPHDGHQXLXJC-UHFFFAOYSA-N 0.000 claims description 2
QZPSOSOOLFHYRR-UHFFFAOYSA-N 3-hydroxypropyl prop-2-enoate Chemical compound OCCCOC(=O)C=C QZPSOSOOLFHYRR-UHFFFAOYSA-N 0.000 claims description 2
239000005057 Hexamethylene diisocyanate Substances 0.000 claims description 2
WOBHKFSMXKNTIM-UHFFFAOYSA-N Hydroxyethyl methacrylate Chemical compound CC(=C)C(=O)OCCO WOBHKFSMXKNTIM-UHFFFAOYSA-N 0.000 claims description 2
ORLQHILJRHBSAY-UHFFFAOYSA-N [1-(hydroxymethyl)cyclohexyl]methanol Chemical compound OCC1(CO)CCCCC1 ORLQHILJRHBSAY-UHFFFAOYSA-N 0.000 claims description 2
238000004132 cross linking Methods 0.000 claims description 2
KORSJDCBLAPZEQ-UHFFFAOYSA-N dicyclohexylmethane-4,4'-diisocyanate Chemical compound C1CC(N=C=O)CCC1CC1CCC(N=C=O)CC1 KORSJDCBLAPZEQ-UHFFFAOYSA-N 0.000 claims description 2
RRAMGCGOFNQTLD-UHFFFAOYSA-N hexamethylene diisocyanate Chemical compound O=C=NCCCCCCN=C=O RRAMGCGOFNQTLD-UHFFFAOYSA-N 0.000 claims description 2
XXMIOPMDWAUFGU-UHFFFAOYSA-N hexane-1,6-diol Chemical compound OCCCCCCO XXMIOPMDWAUFGU-UHFFFAOYSA-N 0.000 claims description 2
SLCVBVWXLSEKPL-UHFFFAOYSA-N neopentyl glycol Chemical compound OCC(C)(C)CO SLCVBVWXLSEKPL-UHFFFAOYSA-N 0.000 claims description 2
229920000728 polyester Polymers 0.000 claims 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 claims description 2
LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 claims 3
PTBDIHRZYDMNKB-UHFFFAOYSA-N 2,2-Bis(hydroxymethyl)propionic acid Chemical compound OCC(C)(CO)C(O)=O PTBDIHRZYDMNKB-UHFFFAOYSA-N 0.000 claims 2
CERQOIWHTDAKMF-UHFFFAOYSA-M Methacrylate Chemical compound CC(=C)C([O-])=O CERQOIWHTDAKMF-UHFFFAOYSA-M 0.000 claims 1
125000004432 carbon atom Chemical group C* 0.000 claims 1
239000003960 organic solvent Substances 0.000 claims 1
239000000203 mixture Substances 0.000 description 7
238000000576 coating method Methods 0.000 description 6
238000010992 reflux Methods 0.000 description 5
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 4
238000007792 addition Methods 0.000 description 4
239000011248 coating agent Substances 0.000 description 4
GMSCBRSQMRDRCD-UHFFFAOYSA-N dodecyl 2-methylprop-2-enoate Chemical compound CCCCCCCCCCCCOC(=O)C(C)=C GMSCBRSQMRDRCD-UHFFFAOYSA-N 0.000 description 4
238000005227 gel permeation chromatography Methods 0.000 description 4
239000003973 paint Substances 0.000 description 4
ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 3
CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 3
239000011230 binding agent Substances 0.000 description 3
239000002904 solvent Substances 0.000 description 3
239000008096 xylene Substances 0.000 description 3
OWYWGLHRNBIFJP-UHFFFAOYSA-N Ipazine Chemical compound CCN(CC)C1=NC(Cl)=NC(NC(C)C)=N1 OWYWGLHRNBIFJP-UHFFFAOYSA-N 0.000 description 2
150000001298 alcohols Chemical class 0.000 description 2
238000005485 electric heating Methods 0.000 description 2
239000012948 isocyanate Substances 0.000 description 2
150000002513 isocyanates Chemical class 0.000 description 2
229910052757 nitrogen Inorganic materials 0.000 description 2
238000010926 purge Methods 0.000 description 2
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
WBIQQQGBSDOWNP-UHFFFAOYSA-N 2-dodecylbenzenesulfonic acid Chemical compound CCCCCCCCCCCCC1=CC=CC=C1S(O)(=O)=O WBIQQQGBSDOWNP-UHFFFAOYSA-N 0.000 description 1
239000004925 Acrylic resin Substances 0.000 description 1
229920000178 Acrylic resin Polymers 0.000 description 1
JIGUQPWFLRLWPJ-UHFFFAOYSA-N Ethyl acrylate Chemical compound CCOC(=O)C=C JIGUQPWFLRLWPJ-UHFFFAOYSA-N 0.000 description 1
239000005058 Isophorone diisocyanate Substances 0.000 description 1
238000005848 Knoop reaction Methods 0.000 description 1
229920000877 Melamine resin Polymers 0.000 description 1
229920003265 Resimene® Polymers 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
150000001412 amines Chemical class 0.000 description 1
150000004945 aromatic hydrocarbons Chemical class 0.000 description 1
125000003118 aryl group Chemical group 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
210000003298 dental enamel Anatomy 0.000 description 1
239000012975 dibutyltin dilaurate Substances 0.000 description 1
238000000113 differential scanning calorimetry Methods 0.000 description 1
229940060296 dodecylbenzenesulfonic acid Drugs 0.000 description 1
230000007613 environmental effect Effects 0.000 description 1
230000001747 exhibiting effect Effects 0.000 description 1
IVJISJACKSSFGE-UHFFFAOYSA-N formaldehyde;1,3,5-triazine-2,4,6-triamine Chemical compound O=C.NC1=NC(N)=NC(N)=N1 IVJISJACKSSFGE-UHFFFAOYSA-N 0.000 description 1
230000009477 glass transition Effects 0.000 description 1
238000010438 heat treatment Methods 0.000 description 1
CATSNJVOTSVZJV-UHFFFAOYSA-N heptan-2-one Chemical compound CCCCCC(C)=O CATSNJVOTSVZJV-UHFFFAOYSA-N 0.000 description 1
239000003999 initiator Substances 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
239000004611 light stabiliser Substances 0.000 description 1
238000000034 method Methods 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
-1 o-phthalic Chemical class 0.000 description 1
PNJWIWWMYCMZRO-UHFFFAOYSA-N pent‐4‐en‐2‐one Natural products CC(=O)CC=C PNJWIWWMYCMZRO-UHFFFAOYSA-N 0.000 description 1
238000006116 polymerization reaction Methods 0.000 description 1
239000007921 spray Substances 0.000 description 1
SWAXTRYEYUTSAP-UHFFFAOYSA-N tert-butyl ethaneperoxoate Chemical compound CC(=O)OOC(C)(C)C SWAXTRYEYUTSAP-UHFFFAOYSA-N 0.000 description 1
239000012974 tin catalyst Substances 0.000 description 1
239000006097 ultraviolet radiation absorber Substances 0.000 description 1

Landscapes

Polyurethanes Or Polyureas (AREA)

CA000527201A 1987-01-13 1987-01-13 Produit de reaction a base d'acrylourethane Expired - Lifetime CA1282888C (fr)

Priority Applications (1)

Application Number	Priority Date	Filing Date	Title
CA000527201A CA1282888C (fr)	1987-01-13	1987-01-13	Produit de reaction a base d'acrylourethane

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
CA000527201A CA1282888C (fr)	1987-01-13	1987-01-13	Produit de reaction a base d'acrylourethane

Publications (1)

Publication Number	Publication Date
CA1282888C true CA1282888C (fr)	1991-04-09

Family

ID=4134741

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CA000527201A Expired - Lifetime CA1282888C (fr)	1987-01-13	1987-01-13	Produit de reaction a base d'acrylourethane

Country Status (1)

Country	Link
CA (1)	CA1282888C (fr)

1987
- 1987-01-13 CA CA000527201A patent/CA1282888C/fr not_active Expired - Lifetime

Legal Events

Date	Code	Title	Description
1999-04-09	MKLA	Lapsed

Publication	Publication Date	Title
US4659780A (en)	1987-04-21	Acrylourethane reaction product
KR100311564B1 (ko)	2001-12-17	내습성수성우레탄/아크릴수지및도료조성물
Athawale et al.	2009	Preparation and properties of urethane/acrylate composite by emulsion polymerization technique
US7196134B2 (en)	2007-03-27	High-solids binder combinations for scratch-resistant topcoats
KR100203561B1 (ko)	1999-06-15	2 성분 수계 가교성 폴리우레탄/아크릴레이트 하이브리드시스템
US5834555A (en)	1998-11-10	Aqueous multicomponent polyurethane coating composition, process for its preparation and its use in methods of producing a multicoat finish
EP0896991B1 (fr)	2003-04-02	Polymères d'acrylates à base de polyesters ou d' oligomères de polyesters, leur préparation et leur utilisation dans des peintures
CA2146480C (fr)	2006-11-28	Compositions de revetement contenant du 1,4-cyclohexane dimethanol
US6001947A (en)	1999-12-14	Coating agent based on a hydroxyl group-containing polyacrylate resin and its use in processes for producing a multicoat paint system
RU2141497C1 (ru)	1999-11-20	Водорастворимые лаковые связующие и способ их получения
US4711929A (en)	1987-12-08	Acrylourethane reaction product
EP0272346B1 (fr)	1992-02-05	Produit de réaction d'acrylo-uréthane
EP0963388A1 (fr)	1999-12-15	Compositions aqueuses durcissables a base d'isocyanate et a faible teneur en composes organiques volatils
WO1998038230A9 (fr)	1999-02-11	Compositions aqueuses durcissables a base d'isocyanate et a faible teneur en composes organiques volatils
EP0852609A1 (fr)	1998-07-15	Peinture a 3 composants avec une haute resistance aux solvants et au decollement
CA1282888C (fr)	1991-04-09	Produit de reaction a base d'acrylourethane
JPH08510287A (ja)	1996-10-29	フルオロポリマーで改質した無水物−エポキシ被覆材組成物
EP1056794A1 (fr)	2000-12-06	Compositions aqueuses durcissables, a base d'isocyanates et a faible teneur en cov
CA2101399C (fr)	1997-12-16	Resine autoreticulable
CA1054285A (fr)	1979-05-08	Preparations filmogenes
JP2661119B2 (ja)	1997-10-08	塗料用樹脂組成物
JPH06329984A (ja)	1994-11-29	物理的迅速乾燥結合剤混合物および木材支持体を塗布するためのそれらの使用
JP3489253B2 (ja)	2004-01-19	塗料用樹脂組成物
JPS63186714A (ja)	1988-08-02	アクリロウレタン反応生成物
JP3000582B2 (ja)	2000-01-17	塗料用樹脂組成物