# US 5,700,344 A · Biodegradable/compostable hot melt adhesives comprising polyester of lactic acid

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- Number: US 5,700,344 A
- Document ID: US5700344A
- Status: Granted
- Kind: A
- Application number: 08/779,291
- Filed: 1997-01-21
- Granted: 1997-12-23
- Earliest claimed: 1993-10-15
- Assignees: H. B. Fuller Licensing & Financing, Inc.
- Inventors: Garry J. Edgington; Christopher M. Ryan
- Web page: https://patentgrep.com/patent/US5700344A

## CPC

- C08L 75/06: from polyesters
- C08G 63/08: Lactones or lactides
- C08L 67/04: Polyesters derived from hydroxycarboxylic acids, e.g. lactones (C08L67/06 takes precedence)
- C08L 75/04: Polyurethanes
- C09J 167/04: Polyesters derived from hydroxycarboxylic acids, e.g. lactones (C09J167/06 takes precedence)
- C08L 2201/06: Biodegradable
- C08L: COMPOSITIONS OF MACROMOLECULAR COMPOUNDS (compositions based on polymerisable monomers C08F, C08G; artificial filaments or fibres D01F; textile treating compositions D06)
- C08G: MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- 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

A hot melt adhesive composition can be made using a polyester derived from 2-propanoic acid (lactic acid). A thermoplastic resin grade polyester can be formulated into a functional adhesive using adhesive components. A lower molecular weight material can be used as a tackifying resin with a biodegradable/compostable resin in a formulated hot melt adhesive. The adhesive material can be made pressure sensitive and can be made entirely by a degradable by combining the polyester polymer with other biodegradable/compostable ingredients. The resulting adhesive composition that can be used in a variety of applications. The biodegradable/compostable adhesive material can be used as a substitute for non-biodegradable materials made from commercial polymers that resist attack by bacteria, fungi and other microbial populations. The hot melt adhesives can be used in (e.g.) packaging and the manufacture of disposable articles which are made from degradable materials. The entire disposable article can be made from adhesives and structural materials that are fully biodegradable/compostable.

## Claims

### Claim 1

A method of using a biodegradable/compostable composition as a hot melt adhesive comprising the steps of:
I. providing a composition comprising:
a) about 10-50 wt-% of biodegradable/compostable thermoplastic resin having a molecular weight (Mn) greater than about 30,000 grams per mole; and
b) about 20-90 wt-% of a biodegradable tackifying resin composition comprising a polylactic acid composition having a molecular weight (Mn) of less than about 20,000 grams per mole and a T.sub.g of less than about 60.degree. C.
II. applying the adhesive to at least one substrate; and
III. forming a bond among the substrates.

### Claim 2 (depends on 1)

The method of claim 1 wherein the adhesive additionally comprises about 1-50 wt-% of a biodegradable/compostable plasticizer.

### Claim 3 (depends on 1)

The method of claim 1 wherein the tackifying resin comprises 40-100 mole-% of L-lactic acid and 0-60 mole-% of D-lactic acid.

### Claim 4 (depends on 2)

The method of claim 2 wherein the plasticizer comprises an ester composition derived from an aromatic or aliphatic mono-, di- or tri-carboxylic acid.

### Claim 5 (depends on 2)

The method of claim 2 wherein the plasticizer comprises a fatty oil.

### Claim 6

A method of using a biodegradable/compostable composition as a hot melt adhesive comprising the steps of:
I. providing a composition comprising:
q) about 10-50 wt-% of a resin grade thermoplastic polylactic acid resin having a molecular weight (Mn) greater than about 30,000 grams per mole; and
r) about 20-90 wt-% of a tackifying resin composition comprising a polymer of lactic acid having a molecular weight (Mn) less than about 20,000 grams per mole and a T.sub.g of about -20.degree. to 60.degree. C.;
II. applying the adhesive to at least one substrate; and
III. forming a bond among the substrates.

### Claim 7 (depends on 6)

The method of claim 6 wherein the thermoplastic resin comprises greater than 90 mole-% lactic acid.

### Claim 8 (depends on 6)

The method of claim 6 wherein the tackifying resin comprises about 95 wt-% of lactic acid monomer and has a T.sub.g of about 0.degree. to 50.degree. C.

### Claim 9 (depends on 6)

The method of claim 6 wherein the T.sub.g of the thermoplastic resin is about 50.degree. to 65.degree. C., the T.sub.g of the tackifying resin is about -10.degree. to 50.degree. C. and the T.sub.g of the adhesive is about -25.degree. C. to 25.degree. C.

### Claim 10 (depends on 6)

The method of claim 6 wherein the adhesive additionally comprises about 1-50 wt-% of a biodegradable/compostable plasticizer.

### Claim 11 (depends on 6)

The method of claim 6 wherein the biodegradable/compostable thermoplastic resin comprises a polymeric material having a molecular weight (Mn) of greater than 40,000 grams per mole.

### Claim 12 (depends on 6)

The method of claim 6 wherein the tackifying resin comprises 50-100 mole-% of L-lactic acid and 0-50 mole-% of D-lactic acid.

### Claim 13 (depends on 6)

The method of claim 6 wherein the tackifying resin comprises 50-95 mole-% of L-lactic acid and 1-50 mole- % of D-lactic acid.

### Claim 14 (depends on 10)

The method of claim 10 wherein the plasticizer comprises an ester composition derived from an aromatic or an aliphatic mono-, di- or tri-carboxylic acid.

### Claim 15

A method of using a biodegradable compostable composition as a hot melt adhesive comprising the steps of:
I. providing a composition comprising:
a) about 10-50 wt-% of a thermoplastic resin selected from the group consisting of a polyester urethane resin having a molecular weight (Mn) greater than 30,000 and a linear polyester resin comprising 1-95 wt-% of a hydroxy butyric acid composition and about 5-35 wt-% of a hydroxy valeric acid composition and mixtures thereof; and
b) about 20-90 wt-% of a tackifying resin composition comprising a polymer of lactic acid having a molecular weight (Mn) less than about 30,000 grams per mole and a T.sub.g of less than 110.degree. C.;
II. applying the adhesive to at least one substrate; and
III. forming a bond among the substrates.

### Claim 16 (depends on 15)

The method of claim 15 wherein the tackifying resin has a T.sub.g of about 10.degree. to 80.degree. C.

### Claim 17 (depends on 15)

The method of claim 15 which additionally comprises about 1-50 wt-% of a compatible biodegradable/compostable plasticizer.

### Claim 18 (depends on 15)

The method of claim 15 wherein the biodegradable/compostable thermoplastic resin comprises a polymeric material having a molecular weight (Mn) of greater than 40,000 grams per mole.

### Claim 19 (depends on 15)

The method of claim 15 wherein the tackifying resin comprises 40-100 mole-% of L-lactic acid and 0-60 mole-% of D-lactic acid having a molecular weight (M.sub.n) less than 20,000 grams per mole.

### Claim 20 (depends on 17)

The method of claim 17 wherein the plasticizer comprises an ester composition derived from an aliphatic or aromatic mono-, di- or tri-carboxylic acid.

### Claim 21 (depends on 1)

The method of claim 1 wherein at least one substrate is a film selected from the group consisting of compostable polylactic acid, compostable polyvinyl alcohol, compostable starch-polycaprolactone and polycaprolactone.

### Claim 22 (depends on 1)

The method of claim 1 wherein at least one substrate is a compostable nonwoven.

### Claim 23 (depends on 22)

The method of claim 22 wherein the compostable nonwoven is a polylactic acid nonwoven.

### Claim 24 (depends on 1)

The method of claim 1 wherein the adhesive is applied to at least one substrate in various applications selected from the group consisting of case and carton sealing, bookbinding, bottle labeling, film laminating and disposable article construction.

### Claim 25 (depends on 24)

The method of claim 24 wherein the disposable articles are selected from the group consisting of infant diapers, incontinent pads and sanitary articles.