CA1240339A - Amine reticulaire polyfonctionnelle, sa fabrication, et produits qui la renferment - Google Patents

Amine reticulaire polyfonctionnelle, sa fabrication, et produits qui la renferment

Info

Publication number: CA1240339A
Authority: CA; Canada
Prior art keywords: amine; carbon atoms; primary amine; polymer; formula
Prior art date: 1983-09-06
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

CA000462352A

Other languages

English (en)

Inventor

Roland Dileone

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.)

Wyeth Holdings LLC

Original Assignee

American Cyanamid 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.)

1983-09-06

Filing date

1984-09-04

Publication date

1988-08-09

1984-09-04 Application filed by American Cyanamid Co filed Critical American Cyanamid Co

1988-08-09 Application granted granted Critical

1988-08-09 Publication of CA1240339A publication Critical patent/CA1240339A/fr

Status Expired legal-status Critical Current

Links

239000000203 mixture Substances 0.000 title claims abstract description 34
238000000034 method Methods 0.000 title claims abstract description 25
150000001412 amines Chemical class 0.000 title abstract description 15
239000004971 Cross linker Substances 0.000 title abstract description 7
239000003431 cross linking reagent Substances 0.000 claims abstract description 22
150000003141 primary amines Chemical class 0.000 claims abstract description 16
238000013035 low temperature curing Methods 0.000 claims abstract description 10
229920013730 reactive polymer Polymers 0.000 claims abstract description 10
229920000642 polymer Polymers 0.000 claims description 34
125000004432 carbon atom Chemical group C* 0.000 claims description 16
239000000178 monomer Substances 0.000 claims description 14
150000002148 esters Chemical class 0.000 claims description 13
239000006227 byproduct Substances 0.000 claims description 8
239000000047 product Substances 0.000 claims description 8
125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 claims description 8
229920002554 vinyl polymer Polymers 0.000 claims description 8
NAQMVNRVTILPCV-UHFFFAOYSA-N hexane-1,6-diamine Chemical group NCCCCCCN NAQMVNRVTILPCV-UHFFFAOYSA-N 0.000 claims description 7
150000005690 diesters Chemical class 0.000 claims description 6
150000004985 diamines Chemical class 0.000 claims description 5
238000004821 distillation Methods 0.000 claims description 4
125000000753 cycloalkyl group Chemical group 0.000 claims description 3
229920006037 cross link polymer Polymers 0.000 claims description 2
125000000217 alkyl group Chemical group 0.000 claims 3
IEPRKVQEAMIZSS-UHFFFAOYSA-N Di-Et ester-Fumaric acid Natural products CCOC(=O)C=CC(=O)OCC IEPRKVQEAMIZSS-UHFFFAOYSA-N 0.000 claims 1
IEPRKVQEAMIZSS-WAYWQWQTSA-N Diethyl maleate Chemical group CCOC(=O)\C=C/C(=O)OCC IEPRKVQEAMIZSS-WAYWQWQTSA-N 0.000 claims 1
LDCRTTXIJACKKU-ARJAWSKDSA-N dimethyl maleate Chemical group COC(=O)\C=C/C(=O)OC LDCRTTXIJACKKU-ARJAWSKDSA-N 0.000 claims 1
238000000576 coating method Methods 0.000 abstract description 9
238000001723 curing Methods 0.000 abstract description 5
239000011248 coating agent Substances 0.000 abstract description 4
230000002194 synthesizing effect Effects 0.000 abstract description 3
150000001875 compounds Chemical class 0.000 abstract 1
238000006243 chemical reaction Methods 0.000 description 24
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 21
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 12
241001315286 Damon Species 0.000 description 11
125000004185 ester group Chemical group 0.000 description 10
229920000180 alkyd Polymers 0.000 description 9
239000002904 solvent Substances 0.000 description 7
SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 description 5
NIXOWILDQLNWCW-UHFFFAOYSA-N 2-Propenoic acid Natural products OC(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 5
238000002360 preparation method Methods 0.000 description 5
239000000376 reactant Substances 0.000 description 5
239000011541 reaction mixture Substances 0.000 description 5
229920005989 resin Polymers 0.000 description 5
239000011347 resin Substances 0.000 description 5
239000007787 solid Substances 0.000 description 5
NEYTXADIGVEHQD-UHFFFAOYSA-N 2-hydroxy-2-(prop-2-enoylamino)acetic acid Chemical compound OC(=O)C(O)NC(=O)C=C NEYTXADIGVEHQD-UHFFFAOYSA-N 0.000 description 4
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 4
QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 4
-1 decorative Substances 0.000 description 4
JMSTYCQEPRPFBF-UHFFFAOYSA-N methyl 2-methoxy-2-(prop-2-enoylamino)acetate Chemical compound COC(=O)C(OC)NC(=O)C=C JMSTYCQEPRPFBF-UHFFFAOYSA-N 0.000 description 4
150000003440 styrenes Chemical class 0.000 description 4
NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 description 3
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Natural products CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 3
LCGLNKUTAGEVQW-UHFFFAOYSA-N Dimethyl ether Chemical group COC LCGLNKUTAGEVQW-UHFFFAOYSA-N 0.000 description 3
VVQNEPGJFQJSBK-UHFFFAOYSA-N Methyl methacrylate Chemical compound COC(=O)C(C)=C VVQNEPGJFQJSBK-UHFFFAOYSA-N 0.000 description 3
208000003251 Pruritus Diseases 0.000 description 3
235000018936 Vitellaria paradoxa Nutrition 0.000 description 3
239000012298 atmosphere Substances 0.000 description 3
239000008199 coating composition Substances 0.000 description 3
238000004132 cross linking Methods 0.000 description 3
125000000118 dimethyl group Chemical group [H]C([H])([H])* 0.000 description 3
WNAHIZMDSQCWRP-UHFFFAOYSA-N dodecane-1-thiol Chemical compound CCCCCCCCCCCCS WNAHIZMDSQCWRP-UHFFFAOYSA-N 0.000 description 3
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 3
125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 3
230000011514 reflex Effects 0.000 description 3
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
WSLDOOZREJYCGB-UHFFFAOYSA-N 1,2-Dichloroethane Chemical class ClCCCl WSLDOOZREJYCGB-UHFFFAOYSA-N 0.000 description 2
AYMDJPGTQFHDSA-UHFFFAOYSA-N 1-(2-ethenoxyethoxy)-2-ethoxyethane Chemical compound CCOCCOCCOC=C AYMDJPGTQFHDSA-UHFFFAOYSA-N 0.000 description 2
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 2
VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 description 2
QIGBRXMKCJKVMJ-UHFFFAOYSA-N Hydroquinone Chemical compound OC1=CC=C(O)C=C1 QIGBRXMKCJKVMJ-UHFFFAOYSA-N 0.000 description 2
CERQOIWHTDAKMF-UHFFFAOYSA-N Methacrylic acid Chemical compound CC(=C)C(O)=O CERQOIWHTDAKMF-UHFFFAOYSA-N 0.000 description 2
239000004952 Polyamide Substances 0.000 description 2
CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
239000002253 acid Substances 0.000 description 2
239000000853 adhesive Substances 0.000 description 2
230000001070 adhesive effect Effects 0.000 description 2
125000001931 aliphatic group Chemical group 0.000 description 2
SNCZNSNPXMPCGN-UHFFFAOYSA-N butanediamide Chemical group NC(=O)CCC(N)=O SNCZNSNPXMPCGN-UHFFFAOYSA-N 0.000 description 2
MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 2
239000000839 emulsion Substances 0.000 description 2
238000010438 heat treatment Methods 0.000 description 2
239000004615 ingredient Substances 0.000 description 2
239000007788 liquid Substances 0.000 description 2
229910052757 nitrogen Inorganic materials 0.000 description 2
229920002647 polyamide Polymers 0.000 description 2
238000006116 polymerization reaction Methods 0.000 description 2
238000010926 purge Methods 0.000 description 2
UBQKCCHYAOITMY-UHFFFAOYSA-N pyridin-2-ol Chemical compound OC1=CC=CC=N1 UBQKCCHYAOITMY-UHFFFAOYSA-N 0.000 description 2
238000001228 spectrum Methods 0.000 description 2
238000003756 stirring Methods 0.000 description 2
VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 2
229920002818 (Hydroxyethyl)methacrylate Polymers 0.000 description 1
JSUIDWXMMPYUCM-UHFFFAOYSA-N 1,10-diaminodecane-4,7-dione Chemical compound NCCCC(=O)CCC(=O)CCCN JSUIDWXMMPYUCM-UHFFFAOYSA-N 0.000 description 1
JIHQDMXYYFUGFV-UHFFFAOYSA-N 1,3,5-triazine Chemical compound C1=NC=NC=N1 JIHQDMXYYFUGFV-UHFFFAOYSA-N 0.000 description 1
WJFKNYWRSNBZNX-UHFFFAOYSA-N 10H-phenothiazine Chemical compound C1=CC=C2NC3=CC=CC=C3SC2=C1 WJFKNYWRSNBZNX-UHFFFAOYSA-N 0.000 description 1
XNWFRZJHXBZDAG-UHFFFAOYSA-N 2-METHOXYETHANOL Chemical compound COCCO XNWFRZJHXBZDAG-UHFFFAOYSA-N 0.000 description 1
ZNQVEEAIQZEUHB-UHFFFAOYSA-N 2-ethoxyethanol Chemical compound CCOCCO ZNQVEEAIQZEUHB-UHFFFAOYSA-N 0.000 description 1
OMIGHNLMNHATMP-UHFFFAOYSA-N 2-hydroxyethyl prop-2-enoate Chemical compound OCCOC(=O)C=C OMIGHNLMNHATMP-UHFFFAOYSA-N 0.000 description 1
GNSFRPWPOGYVLO-UHFFFAOYSA-N 3-hydroxypropyl 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OCCCO GNSFRPWPOGYVLO-UHFFFAOYSA-N 0.000 description 1
QZPSOSOOLFHYRR-UHFFFAOYSA-N 3-hydroxypropyl prop-2-enoate Chemical compound OCCCOC(=O)C=C QZPSOSOOLFHYRR-UHFFFAOYSA-N 0.000 description 1
HRPVXLWXLXDGHG-UHFFFAOYSA-N Acrylamide Chemical compound NC(=O)C=C HRPVXLWXLXDGHG-UHFFFAOYSA-N 0.000 description 1
NLHHRLWOUZZQLW-UHFFFAOYSA-N Acrylonitrile Chemical compound C=CC#N NLHHRLWOUZZQLW-UHFFFAOYSA-N 0.000 description 1
235000009434 Actinidia chinensis Nutrition 0.000 description 1
244000298697 Actinidia deliciosa Species 0.000 description 1
235000009436 Actinidia deliciosa Nutrition 0.000 description 1
VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
239000004593 Epoxy Substances 0.000 description 1
WOBHKFSMXKNTIM-UHFFFAOYSA-N Hydroxyethyl methacrylate Chemical compound CC(=C)C(=O)OCCO WOBHKFSMXKNTIM-UHFFFAOYSA-N 0.000 description 1
238000006957 Michael reaction Methods 0.000 description 1
XTXRWKRVRITETP-UHFFFAOYSA-N Vinyl acetate Chemical compound CC(=O)OC=C XTXRWKRVRITETP-UHFFFAOYSA-N 0.000 description 1
239000003377 acid catalyst Substances 0.000 description 1
239000000654 additive Substances 0.000 description 1
XYLMUPLGERFSHI-UHFFFAOYSA-N alpha-Methylstyrene Chemical class CC(=C)C1=CC=CC=C1 XYLMUPLGERFSHI-UHFFFAOYSA-N 0.000 description 1
XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 1
229910052782 aluminium Inorganic materials 0.000 description 1
125000003277 amino group Chemical group 0.000 description 1
229910052799 carbon Inorganic materials 0.000 description 1
239000003054 catalyst Substances 0.000 description 1
239000007795 chemical reaction product Substances 0.000 description 1
239000003795 chemical substances by application Substances 0.000 description 1
101150116749 chuk gene Proteins 0.000 description 1
230000000052 comparative effect Effects 0.000 description 1
238000009833 condensation Methods 0.000 description 1
230000005494 condensation Effects 0.000 description 1
239000012043 crude product Substances 0.000 description 1
MGNCLNQXLYJVJD-UHFFFAOYSA-N cyanuric chloride Chemical compound ClC1=NC(Cl)=NC(Cl)=N1 MGNCLNQXLYJVJD-UHFFFAOYSA-N 0.000 description 1
239000002274 desiccant Substances 0.000 description 1
230000008034 disappearance Effects 0.000 description 1
AUGNCVYFTKWRBU-UHFFFAOYSA-N ethyl 2-ethoxy-2-(prop-2-enoylamino)acetate Chemical compound C=CC(=O)NC(OCC)C(=O)OCC AUGNCVYFTKWRBU-UHFFFAOYSA-N 0.000 description 1
RYKJYTXKWAAMRT-UHFFFAOYSA-N ethyl 2-methoxy-2-(prop-2-enoylamino)acetate Chemical compound CCOC(=O)C(OC)NC(=O)C=C RYKJYTXKWAAMRT-UHFFFAOYSA-N 0.000 description 1
239000001530 fumaric acid Substances 0.000 description 1
125000000524 functional group Chemical group 0.000 description 1
239000011521 glass Substances 0.000 description 1
150000002391 heterocyclic compounds Chemical class 0.000 description 1
229910052739 hydrogen Inorganic materials 0.000 description 1
239000001257 hydrogen Substances 0.000 description 1
125000004356 hydroxy functional group Chemical group O* 0.000 description 1
238000010952 in-situ formation Methods 0.000 description 1
239000000463 material Substances 0.000 description 1
150000004702 methyl esters Chemical class 0.000 description 1
239000003607 modifier Substances 0.000 description 1
239000002808 molecular sieve Substances 0.000 description 1
URIFRKZNOXMWFA-UHFFFAOYSA-N n,n'-bis(6-aminohexyl)-2-(6-aminohexylamino)butanediamide Chemical group NCCCCCCNC(=O)C(NCCCCCCN)CC(=O)NCCCCCCN URIFRKZNOXMWFA-UHFFFAOYSA-N 0.000 description 1
125000004433 nitrogen atom Chemical group N* 0.000 description 1
229950000688 phenothiazine Drugs 0.000 description 1
239000000049 pigment Substances 0.000 description 1
239000002244 precipitate Substances 0.000 description 1
239000002516 radical scavenger Substances 0.000 description 1
URGAHOPLAPQHLN-UHFFFAOYSA-N sodium aluminosilicate Chemical compound [Na+].[Al+3].[O-][Si]([O-])=O.[O-][Si]([O-])=O URGAHOPLAPQHLN-UHFFFAOYSA-N 0.000 description 1
229910000029 sodium carbonate Inorganic materials 0.000 description 1
239000011877 solvent mixture Substances 0.000 description 1
125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
239000004753 textile Substances 0.000 description 1
238000004448 titration Methods 0.000 description 1
VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 1
239000002023 wood Substances 0.000 description 1

Landscapes

Macromolecular Compounds Obtained By Forming Nitrogen-Containing Linkages In General (AREA)
Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

CA000462352A 1983-09-06 1984-09-04 Amine reticulaire polyfonctionnelle, sa fabrication, et produits qui la renferment Expired CA1240339A (fr)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
US52932483A	1983-09-06	1983-09-06
US529,324		1983-09-06

Publications (1)

Publication Number	Publication Date
CA1240339A true CA1240339A (fr)	1988-08-09

Family

ID=24109441

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CA000462352A Expired CA1240339A (fr)	1983-09-06	1984-09-04	Amine reticulaire polyfonctionnelle, sa fabrication, et produits qui la renferment

Country Status (1)

Country	Link
CA (1)	CA1240339A (fr)

1984
- 1984-09-04 CA CA000462352A patent/CA1240339A/fr not_active Expired

Legal Events

Date	Code	Title	Description
2005-08-09	MKEX	Expiry

Publication	Publication Date	Title
EP0138025B1 (fr)	1989-03-29	Agents de réticulation polyfonctionnels à base d'amines, procédé pour leur préparation et compositions les contenant
US4364876A (en)	1982-12-21	Novel 2-cyanoacrylate, process for producing same and curable composition comprising same
EP0020000B1 (fr)	1983-06-15	Esters activés monomères, polymères préparés à partir de ceux-ci et compositions de revêtement contenant ces polymères
CA1334237C (fr)	1995-01-31	Polymeres contenant des groupes amino, leur preparation et leur utilisation
CA1236631A (fr)	1988-05-10	Preparation des condensee d'uree, et leur emploi
KR0161999B1 (ko)	1999-01-15	거대단량체 연쇄 이동제를 이용한 가교결합성 중합체의 제법
EP0293253A1 (fr)	1988-11-30	Photostabilisants à base d'amines polymères à empêchement stérique
US5332796A (en)	1994-07-26	Organopolysiloxanes and methods for making
AU616886B2 (en)	1991-11-14	Hardenable composition on the basis of a michael addition product, process for the manufacture thereof and use thereof
US4521563A (en)	1985-06-04	Low temperature cure, pigmented coated composition
CA1240339A (fr)	1988-08-09	Amine reticulaire polyfonctionnelle, sa fabrication, et produits qui la renferment
US3974131A (en)	1976-08-10	Aziridine monomers and copolymers
US4528320A (en)	1985-07-09	Low temperature, moisture cure coating composition
CA2149390C (fr)	1999-06-29	Produits d'addition de michael de n-vinylformamide et d'esters acryliques et methacryliques
US4299979A (en)	1981-11-10	Polymerizable monoethylenic carboxylic acids which decarboxylate on heating
EP0310808B1 (fr)	1992-08-05	Compositions durcissables et enduits résistant à la corrosion préparés avec celles-ci
US4530960A (en)	1985-07-23	Low temperature cure, activated ester coating composition with improved pot life
US5294671A (en)	1994-03-15	Monomeric aminoplast crosslinking agents
US6063885A (en)	2000-05-16	Oxazoline or oxazine methacrylate aqueous coating compositions
GB2123407A (en)	1984-02-01	Hydrazides and their use as latent curing agents for epoxy resins
WO1992007823A1 (fr)	1992-05-14	Isocyanates oxime-bloques a base d'isocyanate aliphatique insature tmir (meta)
JPH0217166A (ja)	1990-01-22	エチレン性不飽和尿素誘導体およびその製造方法
KR0171043B1 (ko)	1999-03-30	1,3-디알킬이미다졸-2-티온 촉매를 포함하는 코우팅 조성물
JPH0245642B2 (ja)	1990-10-11	Toryoyojushisoseibutsu
US4260809A (en)	1981-04-07	Copolymerizable, ultraviolet light absorber 4-alkoxy-2'-acryloxy benzazines