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United States Patent (19) 11 Patent Number: 5,753,724 Edgington Et Al

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United States Patent (19) 11 Patent Number: 5,753,724 Edgington Et Al USOO5753724A United States Patent (19) 11 Patent Number: 5,753,724 Edgington et al. 45 Date of Patent: May 19, 1998 54) BIODEGRADABLE/COMPOSTABLE HOT 5,180.765 l/1993 Sinclair ................................... 524/306 MELTADHESIVES COMPRISING 526,050 6/1993 Sinclair ........ ... 524/30 5,252,642 10/1993 Sinclair et al. .. ... 524/320 POLYESTER OF LACTIC ACD 5,252,646 10/1993 Iovine et al. ............................ 524/272 5,32,850 5/1994 Iovine et al. ... 5242 75) Inventors: Garry J. Edgington, White Bear Lake; 5,424,346 6/1995 Sinclair ............ 524/320 Christopher M. Ryan. Dayton, both of 5,444, 13 8/1995 Sinclair et al. ... ... 524/317 Minn. 5,502,158 3/1996 Sinclair et al. ......................... 524/315 73 Assignee: H. B. Fuller Licensing & Financing, Primary Examiner-Peter A. Szekely Inc., St. Paul, Minn. Attorney, Agent, or Firm-Nancy Quan; Carolyn Fischer 57 ABSTRACT 21 Appl. No.: 786,430 A hot melt adhesive composition can be made using a 22 Filed: Jan. 21, 1997 polyester derived from 2-propanoic acid (lactic acid). A thermoplastic resin grade polyester can be formulated into a Related U.S. Application Data functional adhesive using adhesive components. A lower 62 Division of Ser. No. 632,918, Apr. 16, 1996, abandoned, molecular weight material can be used as a tackifying resin which is a continuation of Ser. No. 136,670, Oct. 15, 1993, with a biodegradable/compostable resin in a formulated hot abandoned. melt adhesive. The adhesive material can be made pressure sensitive and can be made entirely by a degradable by (51) Int. Cl. ......................... C08L 67/04: CO8G 63/08; combining the polyester polymer with other biodegradable/ CO8F 120/26 compostable ingredients. The resulting adhesive composi (52) U.S. Cl. .......................... 523/124; 523/125; 523/128: tion that can be used in a variety of applications. The 524/317:524/320: 525/450; 525/415 biodegradable/compostable adhesive material can be used as 58 Field of Search ..................................... 523/124, 125, a substitute for non-biodegradable materials made from 523/126, 127, 128; 524/270. 271. 272, commercial polymers that resist attack by bacteria, fungi and 274, 306. 310, 312, 313, 315, 317, 32O, other microbial populations. The hot melt adhesives can be 322, 294, 296. 297: 525/450. 415: 528/359, used in (e.g.) packaging and the manufacture of disposable 361, 35; 156/327, 336 articles which are made from degradable materials. The entire disposable article can be made from adhesives and 56) References Cited structural materials that are fully biodegradable? U.S. PATENT DOCUMENTS compostable. 4,661.530 4/1987 Gogolewski et al. .................. 521f137 20 Claims, No Drawings 5,753,724 1. 2 BIODEGRADABLE/COMPOSTABLE HOT Nonwovens Industries. Geneva, Switzerland, 1993. MELTADHES WES COMPRISING Accordingly, a substantial need exists to develop POLYESTER OF LACTIC ACD biodegradable/compostable adhesive compositions, particu larly hot melt adhesive compositions comprising a thermo This application is a division of U.S. Ser. No. 08/632,918 plastic resin, a tackifier and a plasticizer (each fully filed Jun. 16, 1996 now abandoned which is a continuation biodegradable/compostable) that can be blended in a hot Of U.S. Ser, No. 08/136,670 filed Oct. 5, 1993 low aban melt product to obtain adhesive, preferably pressure sensi doned, tive adhesive properties. FIELD OF THE INVENTION O BRIEF DESCRIPTION OF THE INVENTION The invention relates to biodegradable/compostable adhe We have found a biodegradable/compostable tackifying sive compositions that are useful in a variety of applications. resin, having a molecular weight less than 30,000, prefer The adhesives can take virtually any form, but preferably are ably less than 20,000 based on 2-hydroxy propanoic acid used as hot melt adhesives. Such adhesives can be used in (lactic acid) that can be combined with biodegradable/ applications including case and carton sealing. book 5 compostable polymers or resins to form fully formulated binding, bottle labeling, film laminating, etc. More biodegradable/compostable hot melt adhesives and hot melt particularly, the adhesives can be formulated to produce hot pressure sensitive adhesives. We have further found classes melt pressure sensitive properties and can be applied in the of biodegradable/compostable thermoplastic resins having a construction of disposable articles including infant diapers. molecular weight greater than 30,000, that can be used with incontinent pads and sanitary applications. the tackifier of the invention. Such resins include but are not limited to a high molecular weight polylactic acid polymer. BACKGROUND OF THE INVENTION a polyester urethane or a high molecular weight PHBV Adhesive compositions are commonly manufactured by polymer. Further, we have identified compatible small mol combining thermoplastic resins or similar polymeric mate 25 ecule compostable plasticizers that can be combined with rials with available plasticizers, tackifiers and other addi the compostable thermoplastic resins and the tackifying tives to produce a wide range of adhesive properties. Com resins of the invention. mon tackifiers or plasticizers are petroleum based or are In the broadest aspect of the invention, we have found that derived from naturally occurring feedstocks, such as wood, the polylactic acid (PLA) material can be useful as an tall oil rosin and terpenes. Synthetic resin materials used in 30 adhesive (used on a 100 wt-% basis) or as a resin or tackifier these adhesives include vinyl resins such as polyethylene or component in adhesive compositions and can provide a polypropylene; a variety of polyester resins; polycarbonate variety of useful properties. If combined with other degrad materials; block copolymers such as styrene isoprene able or compostable materials. the fully formulated adhesive styrene, styrene butadiene styrene, and similar resins. Syn can be biodegradable/compostable in appropriate environ thetic resin technology has become very advanced. 35 ments. Typically, these polymeric resins are usually made from A first aspect of the invention resides in the petroleum sources, have attractive fiber and structural biodegradable/compostable tackifying resin, based on a properties, are low in cost and are easily processed. Formu PLA. Preferred materials have a molecular weight of less lation technology for the manufacture of a variety of blended than or equal to 30,000, preferably less than 20,000 grams useful products is well advanced. Many synthetic resin 40 per mole comprising 2-hydroxy propanoic acid. Further, the materials can be biodegradable/compostable and can be tackifying resins can be modified to improve their tackifying recycled. However, the chemical nature of the materials used utility in adhesive compositions. Lactic acid can act directly in the formulation HMAs is such that no currently available as a food source for microbial populations. The tackifying blend of the resin or polymer material with other compo resins containing substantial amounts of lactic acid are nents is fully subject to degradation by microbial popula 45 directly degradable/compostable. tions in the biodegradable/compostable context. A substan A second aspect of the invention provides a thermoplastic tial need has arisen for adhesives and, in particular, hot melt resin used in the formulation of biodegradable/compostable adhesives that are biodegradable/compostable in the appro hot melt adhesive. Such thermoplastic resins include, but are priate environment including municipal composting facili not limited to: (1) a thermoplastic polylactic acid polymer ties. SO resin, (2) a resin grade or high molecular weight thermo One effort to manufacture partially biodegradable/ plastic polyester such as a polyester urethane, or (3) a compostable adhesives is disclosed in Kauffmann et al., U.S. thermoplastic PHBV polymer with the tackifying resin of Pat. No. 5,169,889, which discloses a hot melt adhesive the invention. Such adhesive compositions can also be composition made by combining a linear polyester compris manufactured using fully biodegradable/compostable ing 3-hydroxybutyric acid and 3-hydroxy pentanoic acid 55 2-hydroxy-propionic acid based tackifiers which we have (3-hydroxy valeric acid) (PHBV). These PHBV materials identified as fully degradable. Edgington, G. J. M. known under the tradename BIOPOL(E) are sold by Zeneca. Mulligan, Compostable Hot Melt Adhesives: An Update, The PHBV polymers are versatile polymers that are envi Paper presented at the Insight 93 International conferences, ronmentally degradable. The PHBV polymer containing Toronto Canada 1993. The fully formulated biodegradable/ adhesive compositions, disclosed in Kauffmann et al... are compostable adhesive compositions can comprise from not fully biodegradable/compostable because of other mate 10-90 wt-% of the 2-hydroxy propanoic acid based tacki rials in the polymer blend. Both non-biodegradable tackif fying resins of the invention; 10-50% of a thermoplastic ers and plasticizers are used. These adhesive formulations polyester urethane, a polylactic acid resin (Mn greater than can still resist substantial biodegradation because of the 20,000 grams per mole) or a PHBV thermoplastic resin presence of non-degradable components. Edgington, G. J. 65 containing 5-35 wt-% of the hydroxy valerate component; Ryan, L. L. Biodegradable Hot Melt Adhesives. Paper 0-45 wt-% of degradable compostable ester plasticizer; and Presented at the INDEX 93 International Congress for the
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