End use applications of biodegradable polymers

• US 5,760,118 A
• Filed: 06/05/1995
• Issued: 06/02/1998
• Est. Priority Date: 08/08/1988
• Status: Expired due to Term

• Current Assignee: NatureWorks LLC (Cargill, Inc. (Agricultural Services Division))
• Original Assignee: Chronopol, Inc.
• Inventors: Rogers, Thomas A., Bigg, Donald, Browning, James D., Lipinsky, Edward S., Sinclair, Richard G.
• Primary Examiner(s): Cain, Edward J.
• Application Number:
  US08/465,462
• Time in Patent Office: 1,093 Days
• Field of Search: 524/306, 524/310, 524/315, 524/317, 524/320, 523/124, 528/354, 528/361
• US Class Current: 524/306
• CPC Class Codes: A61L 15/26 Macromolecular compounds obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds; Derivatives thereof A61L15/225 takes precedence
• CPC Class Codes: A61L 15/62 Compostable, hydrosoluble or hydrodegradable materials
• CPC Class Codes: B01J 2219/1942 spherical
• CPC Class Codes: C08G 63/08 Lactones or lactides
• CPC Class Codes: C08J 2367/04 Polyesters derived from hydroxy carboxylic acids, e.g. lactones C08J2367/06 takes precedence
• CPC Class Codes: C08J 5/18 Manufacture of films or sheets
• CPC Class Codes: C08K 5/10 Esters; Ether-esters
• CPC Class Codes: C08K 5/101 of monocarboxylic acids
• CPC Class Codes: C08L 101/00 Compositions of unspecified macromolecular compounds
• CPC Class Codes: C08L 2666/02 Organic macromolecular compounds, natural resins, waxes or and bituminous materials
• CPC Class Codes: C08L 2666/14 Macromolecular compounds according to C08L59/00 - C08L87/00; Derivatives thereof
• CPC Class Codes: C08L 2666/18 Polyesters or polycarbonates according to C08L67/00 - C08L69/00; Derivatives thereof
• CPC Class Codes: C08L 2666/26 Natural polymers, natural resins or derivatives thereof according to C08L1/00 - C08L5/00, C08L89/00, C08L93/00, C08L97/00 or C08L99/00
• CPC Class Codes: C08L 2666/28 Non-macromolecular organic substances
• CPC Class Codes: C08L 29/00 Compositions of homopolymers or copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by an alcohol, ether, aldehydo, ketonic, acetal or ketal radical; Compositions of hydrolysed polymers of esters of unsaturated alcohols with saturated carboxylic acids; Compositions of derivatives of such polymers
• CPC Class Codes: C08L 53/00 Compositions of block copolymers containing at least one sequence of a polymer obtained by reactions only involving carbon-to-carbon unsaturated bonds; Compositions of derivatives of such polymers
• CPC Class Codes: C08L 57/00 Compositions of unspecified polymers obtained by reactions only involving carbon-to-carbon unsaturated bonds
• CPC Class Codes: 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
• CPC Class Codes: C08L 67/025 containing polyether sequences
• CPC Class Codes: C08L 67/04 Polyesters derived from hydroxycarboxylic acids, e.g. lactones C08L67/06 takes precedence
• CPC Class Codes: C09D 167/04 : Polyesters derived from hydroxycarboxylic acids, e.g. lactones C09D167/06 takes precedence
• CPC Class Codes: 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
• CPC Class Codes: C09J 167/04 : Polyesters derived from hydroxycarboxylic acids, e.g. lactones C09J167/06 takes precedence
• CPC Class Codes: D21H 17/53 : Polyethers; Polyesters

Abstract

Disclosed are products made of degradable materials which include a hydrolytically degradable polymer. The degradable materials can be internally or externally modified. The internally modified polymer composition has polymers modified by the use of comonomers having a relatively high molecular weight. The externally modified polymer composition includes a modifier, wherein the modifier is compatible with the polymer and the modifier is nontoxic, nonvolatile and nonfugitive. The various degradable materials include films, fibers, extruded and molded products, laminates, foams, powders, nonwovens, adhesives and coatings. The disclosed materials are particularly useful for the production of a variety of products in high volumes which are suitable for recycling after use or which are discarded into the environment in large volumes.

Claims

1. A paper product comprising paper fibers and a polymer composition comprising a hydrolytically degradable polymer and a modifier, wherein said modifier is compatible with said polymer and is non-volatile and non-fugitive and wherein said polymer comprises repeating monomer or comonomer units selected from the group consisting of:

##STR17## wherein X is the same or different and is O or NR'"'"' with R'"'"' being the same or different and being H, hydrocarbyl, or substituted hydrocarbyl;

R₁, R₂, R₃ and R₄ can be the same or different and are hydrogen, hydrocarbyl containing 1 to 24 carbon atoms, or substituted hydrocarbyl containing 1 to 24 carbon atoms, and where n₁ and n₂ can be the same or different and are an integer of from 1-12; and

wherein said paper fibers and said polymer composition are configured as a paper product.

2. The paper product of claim 1, wherein said degradable polymer comprises polylactic acid.

3. The paper product of claim 1, wherein said degradable polymer comprises at least about 50 weight percent repeating units derived from lactic acid or lactide.

4. A paper product comprising paper fibers and a polymer composition comprising a hydrolytically degradable polymer, said polymer comprising:

(a) a backbone chain;

(b) first repeating units of the formula ##STR18## where, independently for each such first repeating unit;

X₁ and X₂ are independently O or NR'"'"' and R'"'"' is independently H, hydrocarbyl, substituted hydrocarbyl or a hydrocarbyl derivative;

R₁, R₂ and Z₁ combined have at most one carbon atom;

R₃, R₄ and Z₂ combined have at most one carbon atom;

Z₁ and Z₂ are each independently one or more constituent group extending from the backbone chain and being covalently bonded to an associated carbon atom in the backbone chain, at least one of Z₁ and Z₂ being oxygen which forms a carbonyl group with the associated carbon atom in the backbone chain; and

the molecular weight of such a first repeating unit is less than about 145; and

(c) from about 1 weight percent to about 50 weight percent, based on the total weight of said polymer, of second repeating units of the formula ##STR19## where, independently for each such second repeating unit;

X₃ and X₄ are independently O or NR'"'"' and R'"'"' is independently H, hydrocarbyl, substituted hydrocarbyl or a hydrocarbyl derivative;

R₅, R₆, R₇ and R₈ combined have at least four carbon atoms;

Z₃ and Z₄ are each independently one or more constituent group extending from the backbone chain and being covalently bonded to an associated carbon atom in the backbone chain, at least one of Z₃ and Z₄ being oxygen which forms a carbonyl group with the associated carbon atom in the backbone chain; and

wherein said paper fibers and said polymer composition are configured as a paper product.

5. The paper product of claim 4, wherein said first repeating units are derived from lactic acid or lactide.

6. An absorbent article comprising an absorbent material having the ability to absorb at least about 50 percent by weight of said material'"'"'s weight in water and a polymer composition comprising a hydrolytically degradable polymer and a modifier wherein said modifier is compatible with said polymer and is non-volatile and non-fugitive and wherein said polymer comprises repeating monomer or comonomer units selected from the group consisting of:

##STR20## wherein X is the same or different and is O or NR'"'"' with R'"'"' being the same or different and being H, hydrocarbyl, or substituted hydrocarbyl;

R₁, R₂, R₃ and R₄ can be the same or different and are hydrogen, hydrocarbyl containing 1 to 24 carbon atoms, or substituted hydrocarbyl containing 1 to 24 carbon atoms, and where n₁ and n₂ can be the same or different and are an integer of from 1-12; and

wherein said absorbent material and said polymer composition are configured as an article selected from the group consisting of a towel, napkin, sponge, seed mat, seed strip, tissue and toilet paper.

7. The absorbent article of claim 6, wherein said degradable polymer comprises polylactic acid.

8. The absorbent article of claim 6, wherein said degradable polymer comprises at least about 50 weight percent repeating units derived from lactic acid or lactide.

9. An absorbent article comprising an absorbent material having the ability to absorb at least about 50 percent by weight of said material'"'"'s weight in water and a polymer composition comprising a hydrolytically degradable polymer, said polymer comprising:

(a) a backbone chain;

(b) first repeating units of the formula ##STR21## where, independently for each such first repeating unit;

X₁ and X₂ are independently O or NR'"'"' and R'"'"' is independently H, hydrocarbyl, substituted hydrocarbyl or a hydrocarbyl derivative;

R₁, R₂ and Z₁ combined have at most one carbon atom;

R₃, R₄ and Z₂ combined have at most one carbon atom;

Z₁ and Z₂ are each independently one or more constituent group extending from the backbone chain and being covalently bonded to an associated carbon atom in the backbone chain, at least one of Z₁ and Z₂ being oxygen which forms a carbonyl group with the associated carbon atom in the backbone chain; and

the molecular weight of such a first repeating unit is less than about 145; and

(c) from about 1 weight percent to about 50 weight percent, based on the total weight of said polymer, of second repeating units of the formula ##STR22## where, independently for each such second repeating unit;

X₃ and X₄ are independently O or NR'"'"' and R'"'"' is independently H, hydrocarbyl, substituted hydrocarbyl or a hydrocarbyl derivative;

R₅, R₆, R₇ and R₈ combined have at least four carbon atoms;

Z₃ and Z₄ are each independently one or more constituent group extending from the backbone chain and being covalently bonded to an associated carbon atom in the backbone chain, at least one of Z₃ and Z₄ being oxygen which forms a carbonyl group with the associated carbon atom in the backbone chain; and

wherein said absorbent material and said polymer composition are configured as an absorbent article.

10. The absorbent article of claim 9, wherein said first repeating units are derived from lactic acid or lactide.