Back to results
US 2025/0163295 A1Published application
Coating composition containing tmcd polyester and malonic polyester
AssigneeEastman Chemical Company
InventorsJohn Thorton Maddox, Cameron Lee Brown, Selene Ayde De Leon Ibarra, Linqian Feng, Goliath Beniah, Thauming Kuo
Life of this patent
Estimating the term…
Abstract
This invention pertains to coating compositions based on a blend of polyester containing 2,2,4,4-tetramethyl-1,3-cyclobutanediol (TMCD) and malonic polyester. Coatings based on such polyester blends are capable of providing a good balance of the desirable coating properties, such as solvent resistance, retort resistance, microcracking resistance, and bending ability, for metal packaging applications.
Claims20
A coating composition for metal packaging application, comprising:
- a. a 2,2,4,4-tetramethyl-1,3-cyclobutanediol (TMCD) polyester, which is the reaction product of the monomers comprising:
- i. TMCD in an amount of 35-80 mole %, based on the total moles of (a)(i-iv),
- ii. 1,4-cyclohexanedimethanol (1,4-CHDM) in an amount of 20-65 mole %, based on the total moles of (a)(i-iv),
- iii. a diol other than TMCD and other than 1,4-CHDM in an amount of 0-25 mole %, based on the total moles of (a)(i-iv),
- iv. trimethylolpropane (TMP) in an amount of 0-5 mole %, based on the total moles of (a)(i-iv),
- v. an aromatic diacid in an amount of 90-100 mole %, based on the total moles of (a)(v-vi), and
- vi. an aliphatic diacid in an amount of 0-10 mole %, based on the total moles of (a)(v-vi),
- b. a malonic polyester, which is the reaction product of the monomers comprising:
- i. a cycloaliphatic diol in an amount of 50-100 mole %, based on the total moles of (b)(i-iii),
- ii. an acyclic aliphatic diol in an amount of 0-50 mole %, based on the total moles of (b)(i-iii),
- iii. a triol in an amount of 0-20 mole %, based on the total moles of (b)(i-iii),
- iv. malonic acid, its ester, or a combination thereof, in an amount of 30-100 mole %, based on the total moles of (b)(iv-vi),
- v. an aromatic diacid in an amount of 0-70 mole %, based on the total moles of (b)(iv-vi),
- vi. an aliphatic diacid in an amount of 0-30 mole %, based on the total moles of (b)(iv-vi), and
- c. one or more crosslinkers selected from the group consisting of resole phenolic resin, isocyanate, amino resin crosslinkers, and mixtures thereof,
- wherein said TMCD polyester has a glass transition temperature (Tg) of 60-110° C., an acid number of 0-8 mg KOH/g, a hydroxyl number of 3-25 mg KOH/g, a number average molecular weight (Mn) of 5,000-20,000 g/mole, and a weight average molecular weight (Mw) of 10,000-100,000 g/mole;
- wherein said malonic polyester has a Tg of −20-60° C., an acid number of 0-10 mg KOH/g, a hydroxyl number of 20-80 mgKOH/g, an Mn of 2,000-10,000 g/mole, and an Mw of 5,000-50,000 g/mole.
14 more elements
A coating composition for metal packaging application, comprising:
- a. a 2,2,4,4-tetramethyl-1,3-cyclobutanediol (TMCD) polyester in an amount of 85-95 weight % based on the total weight of (a) and (b), which is the reaction product of the monomers comprising:
- i. TMCD in an amount of 35-80 mole %, based on the total moles of (a)(i-iv),
- ii. 1,4-cyclohexanedimethanol (1,4-CHDM) in an amount of 20-65 mole %, based on the total moles of (a)(i-iv),
- iii. a diol other than TMCD and other than 1,4-CHDM in an amount of 0-25 mole %, based on the total moles of (a)(i-iv),
- iv. trimethylolpropane (TMP) in an amount of 0-5 mole %, based on the total moles of (a)(i-iv),
- v. an aromatic diacid in an amount of 90-100 mole %, based on the total moles of (a)(v-vi), and
- vi. an aliphatic diacid in an amount of 0-10 mole %, based on the total moles of (a)(v-vi),
- b. a malonic polyester in an amount of 5-15 weight % based on the total weight of (a) and (b), which is the reaction product of the monomers comprising:
- i. TMCD or 1,4-CHDM or a combination thereof in an amount of 85-100 mole %, based on the total moles of (b)(i-ii),
- ii. 2-methyl-1,3-propanediol (MPdiol) in an amount of 0-15 mole %, based on the total moles of (b)(i-ii),
- iii. malonic acid, its ester, or a combination thereof, in an amount of 85-100 mole %, based on the total moles of (b)(iii-iv), and
- iv. isophthalic acid (IPA) in an amount of 0-15 mole %, based on the total moles of (b)(iii-iv),
- c. a resole phenolic resin in an amount of 15-30 weight % based on the total weight of (a), (b), (c), and (d), and
- d. isophorone diisocyanate (IPDI) in an amount of 5-15 weight % based on the total weight of (a), (b), (c), and (d),
- wherein said TMCD polyester has a glass transition temperature (Tg) of 60-110° C., acid number of 0-8 mg KOH/g), hydroxyl number of 3-25 mgKOH/g, number average molecular weight (Mn) of 5,000-20,000 g/mole, and weight average molecular weight (Mw) of 10,000-100,000 g/mole;
- said malonic polyester has a Tg of −20 to 20° C., acid number of 0-10 mg KOH/g, hydroxyl number of 20-100 mgKOH/g, Mn of 2,000-10,000 g/mole, and Mw of 10,000-150,000 g/mole;
- and wherein said coating has a solvent resistance of greater than 70 MEK double rubs as measured by ASTM D7835 and a wedge bend resistance (% pass) of 60-100 as measured by the method of ASTM D3281.
14 more elements
A coating composition for metal packaging application, comprising:
- a. a 2,2,4,4-tetramethyl-1,3-cyclobutanediol (TMCD) polyester in an amount of 85-95 weight % based on the total weight of (a) and (b), which is the reaction product of the monomers comprising:
- i. TMCD in an amount of 35-80 mole %, based on the total moles of (a)(i-iv),
- ii. 1,4-cyclohexanedimethanol (1,4-CHDM) in an amount of 20-65 mole %, based on the total moles of (a)(i-iv),
- iii. a diol other than TMCD and other than 1,4-CHDM in an amount of 0-25 mole %, based on the total moles of (a)(i-iv),
- iv. trimethylolpropane (TMP) in an amount of 0-5 mole %, based on the total moles of (a)(i-iv),
- v. an aromatic diacid in an amount of 90-100 mole %, based on the total moles of (a)(v-vi), and
- vi. an aliphatic diacid in an amount of 0-10 mole %, based on the total moles of (a)(v-vi),
- b. a malonic polyester in an amount of 5-15 weight % based on the total weight of (a) and (b), which is the reaction product of the monomers comprising:
- i. TMCD in an amount of 30-50 mole %, based on the total moles of (b)(i-iii),
- ii. 1,4-CHDM in an amount of 20-40 mole %, based on the total moles of (b)(i-iii),
- iii. 2-methyl-1,3-propanediol (MPdiol) in an amount of 20-40 mole %, based on the total moles of (b)(i-iiI),
- iv. malonic acid, its ester, or a combination thereof, in an amount of 70-85 mole %, based on the total moles of (b)(iv-v), and
- v. isophthalic acid (IPA) in an amount of 15-30 mole %, based on the total moles of (b)(iv-v),
- c. a resole phenolic resin in an amount of 15-30 weight % based on the total weight of (a), (b), (c), and (d), and
- d. isophorone diisocyanate (IPDI) in an amount of 5-15 weight % based on the total weight of (a), (b), (c), and (d),
- wherein said TMCD polyester has a glass transition temperature (Tg) of 60-110° C., acid number of 0-8 mg KOH/g), hydroxyl number of 3-25 mgKOH/g, number average molecular weight (Mn) of 5,000-20,000 g/mole, and weight average molecular weight (Mw) of 10,000-100,000 g/mole;
- said malonic polyester has a Tg of 0 to 40° C., acid number of 0-10 mg KOH/g, hydroxyl number of 20-100 mgKOH/g, Mn of 2,000-10,000 g/mole, and Mw of 10,000-150,000 g/mole;
- and wherein said coating has a solvent resistance of greater than 70 MEK double rubs as measured by ASTM D7835 and a wedge bend resistance (% pass) of 60-100 as measured by the method of ASTM D3281.
15 more elements
Dependencies are inferred from the claim text.