# US 9,517,584 B2 · Articles comprising isosorbide and processes for their manufacture > Agents: this data is available as JSON from the patentgrep API and MCP server — see https://patentgrep.com/llms.txt - Number: US 9,517,584 B2 - Document ID: US9517584B2 - Status: Granted - Kind: B2 - Application number: 14/132,361 - Filed: 2013-12-18 - Published: 2015-06-18 - Granted: 2016-12-13 - Earliest claimed: 2013-12-18 - Assignees: Eastman Chemical Company - Applicants: Eastman Chemical Company - Inventors: Robert Ellis McCrary - Web page: https://patentgrep.com/patent/US9517584B2 ## CPC - C08G 63/672: Dicarboxylic acids and dihydroxy compounds - B29C 49/0006: {for heating or cooling} - B29C 49/0872: {axial stretch ratio} - B29C 49/6418: {Heating of preforms} - C08G 63/199: Acids or hydroxy compounds containing cycloaliphatic rings - B29C 49/0015: {Making articles of indefinite length, e.g. corrugated tubes} - B29C 49/0021: {using moulds or mould parts movable in a closed path, e.g. mounted on movable endless supports} - B29C 49/22: using multilayered preforms or parisons - B29K 2025/06: {PS, i.e. polystyrene} - B29K 2033/08: {Polymers of acrylic acid esters, e.g. PMA, i.e. polymethylacrylate} - B29K 2033/12: {Polymers of methacrylic acid esters, e.g. PMMA, i.e. polymethylmethacrylate} - B29K 2067/00: Use of polyesters {or derivatives thereof}, as moulding material - B29K 2069/00: Use of PC, i.e. polycarbonates {or derivatives thereof}, as moulding material - B29K 2105/0094: {having particular viscosity} - B29L 2031/7158: {Bottles} - C08G: MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS - B29C: SHAPING OR JOINING OF PLASTICS; SHAPING OF MATERIAL IN A PLASTIC STATE, NOT OTHERWISE PROVIDED FOR; AFTER-TREATMENT OF THE SHAPED PRODUCTS, e.g. REPAIRING (making preforms B29B11/00; making laminated products by combining previously unconnected layers which become one product whose layers will remain together B32B37/00 - B32B41/00) - B29K: INDEXING SCHEME ASSOCIATED WITH SUBCLASSES B29B, B29C OR B29D, RELATING TO MOULDING MATERIALS OR TO MATERIALS FOR {MOULDS, } REINFORCEMENTS, FILLERS OR PREFORMED PARTS, e.g. INSERTS - B29L: INDEXING SCHEME ASSOCIATED WITH SUBCLASS B29C, RELATING TO PARTICULAR ARTICLES ## Abstract The invention is generally directed to sports bottles and other articles produced by blow molding from polymeric materials containing isosorbide having glass transition temperatures ranging from 90° C. to 130° C., as well as to processes for producing them. These articles can be exposed to water at high temperatures and can be produced by using a suitable combination of a stretch ratio of less than 3× and a preform temperature at least 20° C. greater than the glass transition temperature (Tg) of the polymeric material. ## Claims ### Claim 1 A process for making a sports bottle comprising blow molding a preform made from a polymeric material, wherein the preform temperature at the time of inflation is at least 20° C. above the Tg temperature of the polymeric material; wherein the stretch ratio of the sports bottle with respect to the preform is 2.7× or less; wherein the Tg of the polymeric material is from 90° C. to 130° C.; wherein the polymeric material is a polyester composition comprising: (I) at least one polyester, which comprises (a) a dicarboxylic acid component comprising: i) 70 to 100 mole % of terephthalic acid residues; ii) 0 to 30 mole % of aromatic dicarboxylic acid residues having up to 20 carbon atoms; and iii) 0 to 10 mole % of aliphatic dicarboxylic acid residues having up to 16 carbon atoms; and (b) a glycol component comprising: i) 5 to 35 mole % of isosorbide residues; ii) 40 to 65 mole % of 1,4-cyclohexanedimethanol residues, and iii) 20 to 45 mole % of ethlylene glycol residues; wherein the total mole % of the dicarboxylic acid component is 100 mole %, and the total mole % of the glycol component is 100 mole %; wherein the inherent viscosity of the polyester is from 0.45 to 1.0 dL/g as determined in 60/40 (wt/wt) phenol/tetrachloroethane at a concentration of 0.5 g/100 ml at 25° C.; and wherein the sports bottle displays shrinkage of 5% or less after immersion in boiling water for one hour. ### Claim 2 (depends on 1) A process according to claim 1, wherein the glycol component of the polyester composition comprises 10 to 30 mole % of isosorbide residues; 45 to 60 mole % of 1,4-cyclohexanedimethanol residues, and 20 to 40 mole % of ethylene glycol residues; wherein the inherent viscosity of the polyester is from 0.50 to 0.80 dL/g as determined in 60/40 (wt/wt) phenol/tetrachloroethane at a concentration of 0.5 g/100 ml at 25° C.; and wherein the polyester has a Tg of from 90 to 130° C. ### Claim 3 (depends on 1) A process according to claim 1, wherein the glycol component of the polyester composition comprises 10 to 25 mole % of isosorbide residues; 45 to 55 mole % of 1,4-cyclohexanedimethanol residues; and 20 to 40 mole % ethylene glycol residues; wherein the inherent viscosity of the polyester is from 0.50 to 0.75 dL/g as determined in 60/40 (wt/wt) phenol/tetrachloroethane at a concentration of 0.5 g/100 ml at 25° C.; and wherein the polyester has a Tg of from 95 to 115°; wherein the inherent viscosity of the polyester is from 0.50 to 0.80 dL/g as determined in 60/40 (wt/wt) phenol/tetrachloroethane at a concentration of 0.5 g/100 ml at 25° C.; and wherein the polyester has a Tg of from 118 to 122° C. ### Claim 4 (depends on 1) A process according to claim 1, wherein the preform temperature at the time of inflation is at least 30° C. above the Tg temperature of the polymeric material. ### Claim 5 (depends on 1) A process according to claim 1, wherein the preform temperature at the time of inflation is from 30° C. above the Tg temperature of the polymeric material to 70° C. above the Tg temperature of the polymeric material. ### Claim 6 (depends on 1) A process according to claim 1, wherein the stretch ratio of the bottle with respect to the preform is from 1.2× to 2.7×. ### Claim 7 (depends on 1) A process according to claim 1, wherein the stretch ratio of the bottle with respect to the preform is from 1.2× to 2.5×. ### Claim 8 (depends on 1) A process according to claim 1, wherein the stretch ratio of the bottle with respect to the preform is from 1.2× to 2.0×. ### Claim 9 (depends on 1) A process according to claim 1, wherein the stretch ratio of the bottle with respect to the preform is from 1.3× to 1.7×. ### Claim 10 (depends on 1) A process according to claim 1, wherein the Tg of the polymeric material is from 95° C. to 130° C. ### Claim 11 (depends on 1) A process according to claim 1, wherein the Tg of the polymeric material is from 95° C. to 125° C. ### Claim 12 (depends on 1) A process according to claim 1, wherein the Tg of the polymeric material is from 100° C. to 130° C. ### Claim 13 (depends on 1) A process according to claim 1, wherein the sports bottle has a shrinkage of 4% or less after immersion in boiling water for one hour. ### Claim 14 (depends on 1) A process according to claim 1, wherein the sports bottle has a shrinkage of 3% or less after immersion in boiling water for one hour. ### Claim 15 (depends on 1) A process according to claim 1, wherein the sports bottle has a shrinkage of 2% or less after immersion in boiling water for one hour. ### Claim 16 (depends on 1) A process according to claim 1, wherein the sports bottle has a shrinkage of 1% or less after immersion in boiling water for one hour. ### Claim 17 (depends on 1) A process according to claim 1, wherein the sports bottle has a haze of 3% or less after immersion in boiling water for one hour. ### Claim 18 (depends on 1) A process according to claim 1, wherein a side wall of the sports bottle has a haze of 2% or less after immersion in boiling water for one hour. ### Claim 19 (depends on 1) A process according to claim 1, wherein a side wall of the sports bottle has a haze of 1% or less after immersion in boiling water for one hour. ### Claim 20 (depends on 1) A process according to claim 1, wherein a side wall of the sports bottle has a haze of 1% or less after immersion in boiling water for one hour. ### Claim 21 (depends on 1) A process according to claim 1, wherein a side wall of the sports bottle has a haze of 1% or less after immersion in boiling water for one hour. ### Claim 22 (depends on 1) A process according to claim 1, wherein a side wall of the sports bottle has a birefringence of 0.02 or less. ### Claim 23 (depends on 1) A process according to claim 1, wherein a side wall of the sports bottle has a birefringence of 0.015 or less. ### Claim 24 (depends on 1) A process according to claim 1, wherein a side wall of the sports bottle has a birefringence of 0.01 or less. ### Claim 25 A process for making a sports bottle comprising blow molding a preform made from a polyester composition, wherein the preform temperature at the time of inflation is at least 20° C. above the Tg temperature of the polyester composition; wherein the stretch ratio of the sports bottle with respect to the preform is from 1.2× to 2.5×; wherein the Tg of the polyester composition is from 95° C. to 125° C.; wherein the sports bottle displays shrinkage of 5% or less after immersion in boiling water for one hour; wherein the polyester composition comprises: (I) at least one polyester, which comprises (a) a dicarboxylic acid component comprising: i) 70 to 100 mole % of terephthalic acid residues; ii) 0 to 30 mole % of aromatic dicarboxylic acid residues having up to 20 carbon atoms; and iii) 0 to 10 mole % of aliphatic dicarboxylic acid residues having up to 16 carbon atoms; and (b) a glycol component comprising: i) 10 to 30 mole % of isosorbide residues; ii) 40 to 65 mole % of 1,4-cyclohexanedimethanol residues, and iii) 20 to 40 mole % of ethylene glycol residues, wherein the total mole % of the dicarboxylic acid component is 100 mole %, and the total mole % of the glycol component is 100 mole %; wherein the inherent viscosity of the polyester is from 0.50 to 0.80 dL/g as determined in 60/40 (wt/wt) phenol/tetrachloroethane at a concentration of 0.5 g/100 ml at 25° C.