EP0083232A1
Expired / Lapsed
EP
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Aqueous compositions comprising blocked isocyanate crosslinking agent
Assignee: Ford-Werke GmbH
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Filing: 1982-12-24
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Granted: —
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Expires: 2002-12-24
Abstract
Abstract Aqueous coating compositions comprising film forming resin bearing reactive functionality and blocked polyisocyanate crosslinking agent which is at least partially solubilized with organic acid and which is stable at room temperature in the presence of said functinality, but reactive therewith at elevated temperatures. The blocked isocyanate is prepared by (A) reacting (i) organic diisocyanate bearing one isocyanate group which is more reactive than the other and (ii) sufficient active hydrogen containing blocking agent to react with substantially all of said more reactive isocyanate groups; and (B) reacting hydroxy functional amine bearing at least two hydroxyl groups and at least one tertiary amine nitrogen with sufficient reaction product (A) to react substantially all free or unblocked isocyanate groups of reaction product (A) with hydroxyl groups of said amine. Alternatively, the blocked isocyanate is prepared by (A) reacting an excess of organic diisocyanate with dihydroxy functional amine containing at least one tertiary nitrogen to form a isocyanate terminated tertiary amine containing intermediate; and (B) reacting the intermediate of (A) with sufficient active hydrogen containing blocking agent to react with substantially all of the terminal isocyanate groups of the intermediate.
Inventors
- 👤 Panagiotis I. Kordomenos
Bibliographic Details
Application Number
—
Jurisdiction
EP
Data Source
google_patents
Last Synchronized
2026-11-03 07:43
CPC Classifications
C; C08; C08G; C08G18/00; C08G18/06; C08G18/28; C08G18/40; C08G18/64; C08G18/6415; C08G18/643; C08G18/08; C08G18/0804; C08G18/0809; C08G18/0814; C08G18/70; C08G18/72; C08G18/80; C08G18/8003; C08G18/8006; C08G18/8041; C08G18/8061; C09; C09D; C09D5/00; C09D5/44; C09D5/4488; C09D5/4496
Claims Analysis
Total Claims: 22
Claim 1
Independent Claim
109 words
An aqueous coating. composition comprising a film-forming resin bearing reactive functionality and a blocked polyisocyanate crosslinking agent capable of reacting with the reactive functionality at elevated temperatures, characterised in that the crosslinking agent comprises an organic diisocyanate in which one isocyanate group has been blocked with a blocking agent containing reactive hydrogen, and the other isocyanate group has been reacted with an hydroxy group of an hydroxy functional amine containg at least two hydroxy groups and atleast one tetiary nitrogen, and in that the crosslinking agent is at least partially solubilised or dispersed in the aqueous composition by an organic acid which protonates at atoms of the crosslinking agent.
Claim 2
Dependent Claim
109 words
An aqueous coating. composition comprising a film-forming resin bearing reactive functionality and a blocked polyisocyanate crosslinking agent capable of reacting with the reactive functionality at elevated temperatures, characterised in that the crosslinking agent comprises an organic diisocyanate in which one isocyanate group has been blocked with a blocking agent containing reactive hydrogen, and the other isocyanate group has been reacted with an hydroxy group of an hydroxy functional amine containg at least two hydroxy groups and atleast one tetiary nitrogen, and in that the crosslinking agent is at least partially solubilised or dispersed in the aqueous composition by an organic acid which protonates at atoms of the crosslinking agent.
Claim 3
Dependent Claim
32 words
A coating composition in accordance with claim 1 wherein said crosslinking a gent comprises one or more compounds derived from an aliphatic, cycloaliphatic, . or aromatic diisocyanate ., or a hybrid thereof.
Claim 4
Dependent Claim
38 words
A coating composition in accordance with claim 1 or claim 2 wherein said blocking agent comprises (i) an aliphatic, cycloaliphatic or aromatic alkyl monoalcohol, (ii) an oxime, (iii) a lactam, or (iv) a triazole, or a mixture thereof.
Claim 5
Dependent Claim
29 words
A coating composition in accordance with any one of claims 1 to 3 wherein said hydroxy functional amine comprises an aliphatic, cycloaliphatic or aromatic amine or a mixture thereof.
Claim 6
Dependent Claim
22 words
A coating composition in accordance with any one of claims 1 to 4 wherein said hydroxy functional amine contains multiple tertiary nitrogens.
Claim 7
Dependent Claim
34 words
A coating composition in accordance with any one of claims 1 to 5 wherein saia hydroxy functional amine contains a single tertiary nitrogen and comprises a diol, or a triol or a mixture thereof.
Claim 8
Dependent Claim
87 words
A coating composition in accordance with claim 6 wherein said hydroxy functional amine comprises a diol or triol represented by the formula wherein R 1 and R 2 represent: (̵CH 2 )̵ n OH, wherein n = 1-5; (̵CH 2 CH 2 O) n CH 2 CH 2 -OH, where n = 1-12; wherein n = 1-12; or where n = 1-12; and k 3 represents a C 1 -C 4 alkyl group or any one of the groups represented by R 1 and R 2 .
Claim 9
Dependent Claim
88 words
A coating composition according to any one of claims 1 to 7 wherein the crosslinking agent is derived from an organic diisocyanate bearing one isocyanate group which is more reactive than the other and is prepared by (A) reacting the organic diisocyanate with sufficient blocking agent to block substantially all of said more reactive isocyanate groups; and (B) reacting the hydroxy functional amine with sufficient reaction product (A) to react substantially all the free or unblocked isocyanate groups of reaction product (A) with hydroxyl groups of said amine.
Claim 10
Dependent Claim
14 words
A coating composition in accordance with claim 8 wherein said organic diisocyanate is aromatic.
Claim 11
Dependent Claim
47 words
A coating composition in accordance with claim 8 or claim 9 wherein said diisocyanate comprises l-isocyanato-(p-phenyl isocyanate) methane; 1-isocyanato-2-p-phenyl isocyanato ethane; 4,4'-diisocyanate0-2-nitro-biphenyl; isophorone didsocyante; or a compound having the formula: wherein R represents methyl, ethyl, t-butyl, chloro, bromomethyl, ethoxy, isobutoxy, isopropyl, trichloromethyl or methoxy or mixture thereof.
Claim 12
Dependent Claim
67 words
A coating composition according to any one of claims I to 7 wherein the crosslinking agent is prepared by (A) reacting an excess of the organic diisocyanate with the hydroxy functional amine to form an isocyanate terminated tertiary amine containing intermediate; and (B) reacting the said intermediate with sufficient of the blocking agent to react with substantially all of the terminal isocyanate groups of the said intermediate.
Claim 13
Dependent Claim
43 words
A coating composition in accordance with claim 11 wherein said organic diisocyanate is an isocyanate terminated polyurethane prepolymer prepared by reacting an excess of an aliphatic, cycloaliphatic or aromatic diisocyanate with a diol having a number average molecular weight up to about 500.
Claim 14
Dependent Claim
57 words
A coating composition in accordance with claim 12 wherein said diol employed comprises an aliphatic diol having the formula HO-(CH 2 ) n -OH, where n = 2-8; a cycloaliphatic diol; a polyester diol of the polycaprolactone type; a polyether diol having the formula H(̵OCH 2 CH 2 )̵OH, where n = 2-8; or a mixture thereof.
Claim 15
Dependent Claim
28 words
A coating composition in accordance with claim 13 wherein said diol comprises 1,4 butane diol; 1,6 hexane diol; neopentyl glycol; 1,5 pentanediol; 1,4 cyclohexanediol; or a mixture thereof.
Claim 16
Dependent Claim
29 words
A coating composition in accordance with any one of claims 12 to 14 wherein said diisocyanate and said diol are reacted in a molar ratio of 1.5-2.0 to 1.
Claim 17
Dependent Claim
33 words
A coating composition in accordance with any one of claims 11 to 15 wherein the hydroxy functional amine contains a single tertiary nitrogen atom and comprises a diol or a mixture of diols.
Claim 18
Dependent Claim
41 words
A coating ccmpositicn in accordance with claim 16 wherein the hydroxy functional amine is of the formula (I) wherein R 1 and R 2 are as defined in claim 8, and R 3 represents a C 1 -C 4 alkyl groups.
Claim 19
Dependent Claim
33 words
A coating composition in accordance with any one of claims 11 to 17 wherein said organic diisocyanate and said hydroxy functional amine are reacted in a molar ratio of from 1:1 to 2:1.
Claim 20
Dependent Claim
59 words
A coating composition in accordance with any one of claims 1 to 16 wherein said composition is adapted to be applied to a substrate-cathode by electrodeposition and wherein both said crosslinking a gent and said film forming resin are solubilsed at least in part by ionisation as a result of protonation of an amine nitrogen by an organic acid.
Claim 21
Dependent Claim
25 words
A coating composition in accordance with any one of claims 1 to 19 wherein the film-forming resin comprises an epoxy/ amine adduct bearing hydroxyl functionality.
Claim 22
Dependent Claim
26 words
A coating composition according to any one of claims 1 to 20 wherein the organic acid has a dissociation constant of at least 10 -5 .
References Cited (Backward Citations)
US4031050A
Cited
FR2319657A1
Cited
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