# US 5,352,740 A · Thermosetting compositions, thermal latent carboxyl compounds and methods of preparation thereof > Agents: this data is available as JSON from the patentgrep API and MCP server — see https://patentgrep.com/llms.txt - Number: US 5,352,740 A - Document ID: US5352740A - Status: Granted - Kind: A - Application number: 07/680,356 - Filed: 1991-04-04 - Granted: 1994-10-04 - Earliest claimed: 1990-04-10 - Assignees: Nippon Oil and Fats Co., Ltd. - Inventors: Masahiro Ishidoya; Kishio Shibato; Keiji Komoto; Kenji Shibamoto; Mitsuyuki Mashita; Osamu Ohe - Web page: https://patentgrep.com/patent/US5352740A ## CPC - C09D 167/00: Coating compositions based on polyesters obtained by reactions forming a carboxylic ester link in the main chain (based on polyester-amides C09D177/12; based on polyester-imides C09D179/08); Coating compositions based on derivatives of such polymers - C08L 67/00: Compositions of polyesters obtained by reactions forming a carboxylic ester link in the main chain (of polyester-amides C08L77/12; of polyester-imides C08L79/08); Compositions of derivatives of such polymers - C09D 163/00: Coating compositions based on epoxy resins; Coating compositions based on derivatives of epoxy resins - C09J 167/00: Adhesives based on polyesters obtained by reactions forming a carboxylic ester link in the main chain (based on polyester-amides C09J177/12; based on polyester-imides C09J179/08); Adhesives based on derivatives of such polymers - C08L 2666/02: Organic macromolecular compounds, natural resins, waxes or and bituminous materials - C09D: COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR (cosmetics A61K; processes for applying liquids or other fluent materials to surfaces, in general, B05D; staining wood B27K5/02; glazes or vitreous enamels C03C; natural resins, French polish, drying-oils, driers, turpentine, per se, C09F; polishing compositions other than French polish, ski waxes C09G; adhesives or use of materials as adhesives C09J; materials for sealing or packing joints or covers C09K3/10; materials for stopping leaks C09K3/12; processes for the electrolytic or electrophoretic production of coatings C25D) - C08L: COMPOSITIONS OF MACROMOLECULAR COMPOUNDS (compositions based on polymerisable monomers C08F, C08G; artificial filaments or fibres D01F; textile treating compositions D06) - C09J: ADHESIVES; NON-MECHANICAL ASPECTS OF ADHESIVE PROCESSES IN GENERAL; ADHESIVE PROCESSES NOT PROVIDED FOR ELSEWHERE; USE OF MATERIALS AS ADHESIVES (preparation of glue or gelatine C09H) ## Abstract Thermosetting composition is excellent in storage stability, useful as one component thermosetting composition, gives cured products having excellent chemical properties, physical properties and weathering resistance and is favorably utilized in coating compositions, ink, adhesive and molded plastics. The thermosetting composition comprises a compound having in the molecule two or more carboxyl groups blocked by a vinyl ether compound, a vinyl thioether compound or a hetero compound having a vinyl type double bond and oxygen or sulfur as the hetero atom, a compound having two or more reactive functional groups which can form a chemical bond with the blocked carboxyl compound by heating and optionally a thermal latent acid catalyst. The blocked carboxyl group of the first compound and the reactive functional group of the second compound may be comprised in the same molecule. ## Claims ### Claim 1 A thermosetting composition which comprises: (A) a compound having in the molecule two or more functional groups of the formula (1): ##STR15## wherein R.sup.1, R.sup.2 and R.sup.3 are respectively selected from the group consisting of a hydrogen atom and an organic group of 1 to 18 carbon atoms, R.sup.4 is an organic group of 1 to 18 carbon atom, Y.sup.1 is selected from the group consisting of an oxygen atom and a sulfur atom and R.sup.3 and R.sup.4 may be bonded with each other to form a heterocyclic structure which comprises Y.sup.1 as the hetero atom component; (B) a compound having in the molecule two or more reactive functional groups which can form a chemical bond with the carboxyl functional groups which are generated from the compound (A) by heating; and, optionally, (C) a thermal latent acid catalyst which is activated during curing of the composition by heating. ### Claim 2 (depends on 1) A thermosetting composition as claimed in claim 1, wherein the reactive functional groups of the compound (B) are at least one kind selected from the group consisting of epoxy group, silanol group, alkoxysilane group, hydroxyl group, amino group, imino group, isocyanate group, blocked isocyanate group, cyclocarbonate group, vinyl ether group, vinyl thioether group, aminomethylol group, alkylated aminomethylol group, acetal group and ketal group. ### Claim 3 (depends on 1, 2) Thermosetting composition as claimed in claim 1 or claim 2, wherein the thermal latent acid catalyst (C) is at least one kind selected from the group consisting of a compound prepared by neutralizing a protonic acid or a Lewis acid with a Lewis base, an ester of a sulfonic acid, an ester of phosphoric acid and an onium compound or a compound prepared by mixing a Lewis acid with trialkyl phosphate. ### Claim 4 (depends on 1, 2) A thermosetting composition as claimed in claim 1 or claim 2, wherein the compound (A) and/or the compound (B) are polymers of .alpha.,.beta.-unsaturated compounds. ### Claim 5 (depends on 1, 2) A thermosetting composition as claimed in claim 1 or claim 2, wherein the compound (A) and/or the compound (B) are polyester resins. ### Claim 6 (depends on 3) A thermosetting composition as claimed in claim 3, wherein the compound (A) and/or the compound (B) are polymers of .alpha.,.beta.-unsaturated compounds. ### Claim 7 (depends on 3) A thermosetting composition as claimed in claim 3, wherein the compound (A) and/or the compound (B) are polyester resins. ### Claim 8 (depends on 1) A thermosetting composition as claimed in claim 1, wherein an equivalent ratio of the functional groups of the compound (A) and the reactive functional groups of the compound (B) is 0.2:1.0 to 1.0:0.2. ### Claim 9 (depends on 1) A thermosetting composition as claimed in claim 1, wherein an amount of the thermal latent acid catalyst is 0.01 to 10 weight parts per 100 weight parts of the total solid component which contains the compound (A) and the compound (B). ### Claim 10 (depends on 8) A thermosetting composition as claimed in claim 8, wherein an amount of the thermal latent acid catalyst is 0.01 to 10 weight parts per 100 weight parts of the total solid component which contains the compound (A) and the compound (B). ### Claim 11 (depends on 1, 8, 9) A thermosetting composition as claimed in claim 1, 8 or 9 wherein the compound (A) has 2 to 50 functional groups of the formula (1) in the molecule. ### Claim 12 (depends on 1, 8, 9) A thermosetting composition as claimed in claim 1, 8 or 9 wherein the compound (B) has 2 to 50 reactive functional groups in the molecule. ### Claim 13 (depends on 1, 8) A thermosetting composition as claimed in claim 1, 8 of 10 wherein the compound (A) is a thermal latent carboxyl compound prepared by a reaction of a polycarboxyl compound prepared by half esterification of a polyol having two or more hydroxyl groups in the molecule and an acid anhydride with a vinyl ether compound, whereby the carboxyl group is transformed into the functional group of the formula (1). ### Claim 14 (depends on 13) A thermosetting composition as claim 13, wherein the polycarboxyl compound has an acid equivalent of not more than 1000 g/mole and a number average molecular weight of not more than 4000. ### Claim 15 (depends on 14) A thermosetting composition as claimed in claim 14, wherein the number average molecular weight of the polycarboxyl compound is not more than 2000. ### Claim 16 (depends on 1, 8, 10) A thermosetting composition as claimed in claim 1, 8 or 10 wherein the compound (B) is a compound having two or more epoxy groups in the molecule. ### Claim 17 (depends on 16) A thermosetting composition as claimed in claim 16, wherein the compound (B) is a polymer of .alpha.,.beta.-unsaturated compound. ### Claim 18 (depends on 1, 8, 10) A thermosetting composition as claimed in claim 1, 8 or 10 wherein the thermal latent acid catalyst is a compound which exhibits an activity at a temperature above 60.degree. C. ### Claim 19 (depends on 1, 8, 10) A thermosetting composition as claimed in claim 1, 8, 10 wherein the thermal latent acid catalyst is a compound prepared by neutralizing a Lewis acid and a Lewis base. ### Claim 20 (depends on 13) A thermosetting composition as claimed in claim 13, wherein the vinyl ether compound is an aliphatic vinyl ether compound having 3 to 10 carbon atoms. ### Claim 21 (depends on 13) A thermosetting composition as claimed in claim 13, wherein the vinyl ether compound is an aliphatic vinyl ether compound having 4 to 10 carbon atoms. ### Claim 22 (depends on 13) A thermosetting composition as claimed in claim 13, wherein the vinyl ether compound is methyl vinyl ether, ethyl vinyl ether, isopropyl vinyl ether, n-propyl vinyl ether, n-butyl vinyl ether, isobutyl vinyl ether, 2-ethylhexyl vinyl ether or cyclohexyl vinyl ether. ### Claim 23 (depends on 22) A thermosetting compound as claimed in claim 22, wherein the compound (B) is a compound having two or more epoxy groups in the molecule. ### Claim 24 (depends on 23) A thermosetting composition as claimed in claim 23, wherein the compound (B) is a polymer of an .alpha.,.beta.-unsaturated compound.