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US 10,563,040 B2Granted
Low-temperature curable compositions
AssigneeEastman Chemical Company
InventorsThauming Kuo, Vasudev R. Bhonde, Phillip Bryan Hall
Life of this patent
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Abstract
This invention pertains to a curable composition comprising a first component having beta-ketoacetate and/or malonate functionalities and a second component having two or more aldehyde functionalities. The compositions can be cured at room temperature or low temperatures to yield crosslinked networks that are capable of providing desirable properties for coating and adhesive applications. The reactive functionalities of beta-ketoacetate, malonate, and aldehyde can be either on polymers as the main binders or on small molecules as the crosslinkers. The curable compositions desirably are either solventless or organic solvent based.
Claims14
A curable composition comprising:
- I. a first component having two or more functional groups selected from the group consisting of β-ketoacetate and malonate functional groups;
- II. a second component vinyl polymer having two or more aldehyde functional groups;
- and
- III. a basic catalyst.
1 more element
A curable composition comprising:
- I. a first component adduct having two or more β-ketoacetate functional groups;
- II. a vinyl polymer having two or more aldehyde functional groups;
- and
- III. a basic catalyst.
1 more element
A curable composition comprising:
- I. a first component acetoacetate functional polyester comprising the residues of
- a. a hydroxyl component comprising:
- i. a diol in an amount ranging from 70 to 100 mole %, based on the total moles of (i) and (ii);
- and
- ii. a polyol in an amount ranging from 0 to 30 mole %, based on the total moles of (i) and (ii);
- b. a carboxyl component comprising a polycarboxylic acid compound, a derivative of polycarboxylic acid compound, or a combination thereof;
- and
- c. an alkyl acetoacetate, a diketene, or a combination thereof in an amount ranging from about 5 to about 50 weight %, based on the total weight of (a), (b), and (c);
- II. a second component having two or more aldehyde functional groups;
- and
- III. a basic catalyst;
- wherein the second component is selected from the group comprising 1,3-cyclohexanedicarboxaldehyde (1,3-CHDAL), 1,4-cyclohexanedicarboxaldehyde (1,4-CHDAL), mixtures of 1,3- and 1,4-CHDAL, 2,6-norbornanedicarboxaldehyde, 2,5-norbornane-dicarboxaldehyde, cyclododecane-1,4,8-tricarbaldehyde, 3,(4-formylcyclohexyl)propanal, and their isomers.
9 more elements
A curable composition comprising:
- I. a polyester comprising the residues of:
- a. a hydroxyl component comprising:
- i. a diol in an amount ranging from 70 to 100 mole %, based on the total moles of (i) and (ii);
- and
- ii. a polyol in an amount ranging from 0 to 30 mole %, based on the total moles of (i) and (ii);
- and
- b. malonic acid, its ester, or a combination thereof;
- and
- c. optionally a carboxyl component, other than malonic acid or its ester, comprising a polycarboxylic acid compound, a derivative of polycarboxylic acid compound, or a combination thereof;
- II. an aldehyde component selected from the group consisting of 1,3-cyclohexanedicarboxaldehyde (1,3-CHDAL), 1,4-cyclohexanedicarboxaldehyde (1,4-CHDAL), mixtures of 1,3- and 1,4-CHDAL, 2,6-norbornanedicarboxaldehyde, 2,5-norbornanedicarboxaldehyde, cyclododecane-1,4,8-tricarbaldehyde, 3,(4-formylcyclohexyl)propanal, and their isomers;
- and
- III. a basic catalyst that is one or more selected from the group consisting of 1,8-diazabicyclo-[5.4.0]undec-7-ene (DBU), 1,5-diazabicyclo[4.3.0]non-5-ene (DBN), 1,5,7-triazabicyclo[4.4.0]dec-5-ene (TBD), 7-methyl-1,5,7-triazabicyclo[4.4.0]dec-5-ene (MTBD), 1,1,3,3-tetramethylguanidine (TMG), 1,4-diazabicyclo[2.2.2]octane (DABCO), triethylamine, N,N-dimethylethanolamine, ammonium hydroxide, triphenyl phosphine, and tributyl phosphine.
9 more elements
A curable composition comprising:
- I. an acetoacetate functional polyester comprising the residues of:
- a. a hydroxyl component comprising:
- i. a diol in an amount ranging from 70 to 100 mole %, based on the total moles of (i) and (ii);
- and
- ii. a polyol in an amount ranging from 0 to 30 mole %, based on the total moles of (i) and (ii);
- b. a carboxyl component comprising a polycarboxylic acid compound, a derivative of polycarboxylic acid compound, or a combination thereof;
- and
- c. an alkyl acetoacetate, a diketene, or a combination thereof in an amount ranging from about 5 to about 50 weight %, based on the total weight of (a), (b), and (c);
- II. an aldehyde component selected from the group consisting of 1,3-cyclohexanedicarboxaldehyde (1,3-CHDAL), 1,4-cyclohexanedicarboxaldehyde (1,4-CHDAL), mixtures of 1,3- and 1,4-CHDAL, 2,6-norbornanedicarboxaldehyde, 2,5-norbornane-dicarboxaldehyde, cyclododecane-1,4,8-tricarbaldehyde, 3,(4-formylcyclohexyl)propanal, and their isomers;
- and
- III. a basic catalyst that is one or more selected from the group consisting of 1,8-diazabicyclo-[5.4.0]undec-7-ene (DBU), 1,5-diazabicyclo[4.3.0]non-5-ene (DBN), 1,5,7-triazabicyclo[4.4.0]dec-5-ene (TBD), 7-methyl-1,5,7-triazabicyclo[4.4.0]dec-5-ene (MTBD), 1,1,3,3-tetramethylguanidine (TMG), 1,4-diazabicyclo[2.2.2]octane (DABCO), triethylamine, N,N-dimethylethanolamine, ammonium hydroxide, triphenyl phosphine, and tributyl phosphine.
8 more elements
Dependencies are inferred from the claim text.