Solventless Adhesive Composition and Process for Making and Use in Forming a Laminate

Abstract

The present disclosure provides a process comprising providing an isocyanate component A comprising a blend of (i) an aromatic isocyanate prepolymer and (ii) an aliphatic isocyanate prepolymer; providing a polyol component B comprising a blend of; (i) a phosphate-functional polyol, (ii) a polyether polyol, and (iii) an element selected from the group consisting of a polyurethane polyol, a polyester polyol and a combination thereof; mixing component A and component B to form a solventless adhesive (SLA) composition, wherein a weight ratio of component A to component B is from 2:1 to 1:1, the SLA composition having a pot life from 30 min to 60 min at 40 C; applying the SLA composition between a first film and a second film to form a raw laminate; and curing the raw laminate to form a laminate product.

Claims

1. A process comprising: providing an isocyanate component A comprising a blend of (i) an aromatic isocyanate prepolymer and (ii) an aliphatic isocyanate prepolymer; providing a polyol component B comprising a blend of; (i) a phosphate-functional polyol, (ii) a polyether polyol, and (iii) an element selected from the group consisting of a polyurethane polyol, a polyester polyol and a combination thereof; mixing component A and component B to form a solventless adhesive (SLA) composition, wherein a weight ratio of component A to component B is from 2:1 to 1:1, the SLA composition having a pot life from 30 min to 60 min at 40° C.; applying the SLA composition between a first film and a second film to form a raw laminate; and curing the raw laminate to form a laminate product.

2. The process of claim 1, comprising providing component A comprising a blend from 90 wt % to 80 wt % of the aromatic isocyanate prepolymer and from 10 wt % to 20 wt % of the aliphatic isocyanate prepolymer, based on a total weight of component A.

3. The process of claim 1, comprising providing component B wherein the phosphate-functional polyol is present in an amount from 6 wt % to 16 wt %, based on a total weight of component B.

4. The process of claim 1, comprising forming the SLA composition wherein the phosphate-functional polyol is present in an amount from 4 wt % to 7 wt %, based on a total weight of the SLA composition.

5. The process of claim 1, wherein the first film is composed of polyethylene terephthalate (PET) and the second film is composed of polyethylene (PE), the process further comprising forming a laminate product having an anti-seal value from 3,415 to 3,960 g/25 mm at 160° C., as measured in accordance with the anti-seal test.

6. The process of claim 5, comprising forming a laminate product having a primary aromatic amine (PAA) level from 0.1 to 1.4 parts per billion (ppb) after 24 hours curing at 25° C. and 50% humidity, as measured in accordance with the PAA decay test.

7. A two-component solventless adhesive (SLA) composition comprising: an isocyanate component A comprising a blend of (i) an aromatic isocyanate prepolymer and (ii) an aliphatic isocyanate prepolymer; a polyol component B comprising a blend of; (i) a phosphate-functional polyol, (ii) a polyether polyol, and (iii) an element selected from the group consisting of a polyurethane polyol, a polyester polyol and a combination thereof; the composition having a weight ratio of component A to component B from 2:1 to 1:1; a pot life from 30 min to 60 min at 40° C.; and a primary aromatic amine decay level from 0.1 pbb to 1.4 pbb after 24 hours curing at 25° C. and 50% humidity.

8. The composition of claim 7, wherein component A comprises a blend from 90 wt % to 80 wt % of the aromatic isocyanate prepolymer and from 10 wt % to 20 wt % of the aliphatic isocyanate prepolymer, based on a total weight of component A.

9. The composition of claim 7, wherein the phosphate-functional polyol is present in an amount from 6 wt % to 16 wt %, based on a total weight of component B.

10. The composition of claim 7, wherein the phosphate-functional polyol is present in an amount from 4 wt % to 7 wt %, based on a total weight of the SLA composition.

11. A laminate product comprising: a first film; a second film; and a solventless adhesive composition disposed between the first film and the second film, the solventless adhesive composition comprising (a) an isocyanate component A comprising a blend of (i) an aromatic isocyanate prepolymer and (ii) an aliphatic isocyanate prepolymer; (b) a polyol component B comprising a blend of (i) a phosphate-functional polyol, (ii) a polyether polyol, and (iii) an element selected from the group consisting of a polyurethane polyol, a polyester polyol and a combination thereof; the composition having a weight ratio of component A to component B from 2:1 to 1:1; a pot life from 30 min to 60 min at 40° C.; and a primary aromatic amine decay level from 0.1 pbb to 1.4 pbb after 24 hours curing at 25° C. and 50% humidity.

12. The laminate product of claim 11, wherein the first film is composed of polyethylene terephthalate (PET) and the second film is composed of polyethylene (PE), the laminate product having a bond strength from 3,415 g/25 mm to 4,000 g/25 mm, as measured in accordance the anti-seal test.

13. The laminate product of claim 11, wherein the first film is composed of polyethylene terephthalate (PET) and the second film is composed of polyethylene (PE), the laminate product having a bond strength from 595 g/25 mm to 850 g/25 mm, as measured in accordance with the rigorous food resistance test.

14. The laminate product of claim 11, wherein the first film is composed of polyethylene terephthalate (PET) and the second film is composed of white pigmented polyethylene, the laminate product having a bond strength from 830 g/25 mm to 900 g/25 mm, as measured in accordance with the rigorous food resistance test.

15. The laminate of claim 11 wherein the first film is a metallized film and the second film is composed of polyethylene (PE), the laminate having a bond strength from 900 g/25 mm to 1020 g/25 mm, as measured in accordance with the rigorous food resistance test.

Description

DETAILED DESCRIPTION

[0036] The present disclosure provides a process. The process includes providing an isocyanate component (A) and providing a polyol component (B). The isocyanate component (A) includes a blend of an aromatic isocyanate prepolymer and an aliphatic isocyanate prepolymer. The polyol component (B) includes (i) a phosphate-functional polyol, (ii) a polyether polyol, and (iii) an element selected from the group consisting of a polyurethane polyol, a polyester polyol and a combination thereof. The process includes mixing component A and component B to form a solventless adhesive (SLA) composition, wherein a weight ratio of component A to component B is from 2:1 to 1:1, the SLA composition having a pot life from 30 min to 60 min at 40° C. The process includes applying the SLA composition between a first film and a second film to form a raw laminate and curing the raw laminate to form a laminate product.

Isocyanate Component A

[0037] The isocyanate component A, (interchangeably referred to as component A), includes an isocyanate prepolymer. The isocyanate prepolymer is the reaction product of a polyisocyanate and at least one polyol. The isocyanate prepolymer is an intermediate in the process of transforming polyisocyanates and polyols into an SLA composition.

[0038] A “polyisocyanate” is a molecule that contains at least two isocyanate groups. The polyisocyanate can be an isocyanate or a polyisocyanate. The polyisocyanate bonds to a polyol in a chemical reaction to form an isocyanate prepolymer. Nonlimiting examples of suitable polyisocyanates include aromatic polyisocyanates, aliphatic polyisocyanates, carbodiimide modified polyisocyanates, and combinations thereof.

[0039] An “aromatic polyisocyanate” is a polyisocyanate containing one or more aromatic rings. Nonlimiting examples of suitable aromatic polyisocyanates include isomers of methylene diphenyl dipolyisocyanate (MDI) such as 4, 4′-MDI, 2, 4′-MDI and 2, 2′-MDI; or modified MDI such as carbodiimide modified MDI or allophanate modified MDI; isomers of toluene-dipolyisocyanate (TDI) such as 2, 4-TDI, 2, 6-TDI; isomers of naphthalene-dipolyisocyanate (NDI) such as 1, 5-NDI; isomers of xylene dipolyisocyanate (XDI), and combinations thereof.

[0040] An “aliphatic polyisocyanate” is a polyisocyanate that is void of, or contains no, aromatic rings. Nonlimiting examples of suitable aliphatic polyisocyanates include isomers of hexamethylene dipolyisocyanate (HDI) such as HDI trimer and HDI biuret, isomers of isophorone dipolyisocyanate (IPDI), and combinations thereof.

[0041] In an embodiment, the polyisocyanate is selected from an aliphatic mono-polyisocyanate, an aliphatic di-polyisocyanate, an aliphatic tri-polyisocyanate, and combinations thereof. In a further embodiment, the polyisocyanate is an aliphatic di-polyisocyanate.

[0042] In an embodiment, the polyisocyanate is a multifunctional aliphatic polyisocyanate with at least two isocyanate groups, or at least three isocyanate groups.

[0043] In an embodiment, the polyisocyanate is selected from an aromatic mono-polyisocyanate, an aromatic di-polyisocyanate, an aromatic tri-polyisocyanate, and combinations thereof. In a further embodiment, the polyisocyanate is an aromatic di-polyisocyanate.

[0044] In an embodiment, the polyisocyanate is a multifunctional aromatic polyisocyanate with at least two isocyanate groups, or at least three isocyanate groups.

[0045] In an embodiment, the aromatic polyisocyanate has a density from 0.9, or 1.11, or 1.12, or 1.13 to 1.14, or 1.15, or 1.4 g/cm.sup.3. In a further embodiment, the aromatic polyisocyanate has a density from 0.9 to 1.4 g/cm.sup.3, or from 1.11 to 1.15 g/cm.sup.3, or from 1.12 to 1.14 g/cm.sup.3. In an embodiment, the aromatic polyisocyanate has a density from 1.125 to 1.135 g/cm.sup.3.

[0046] In an embodiment, the aromatic polyisocyanate has a viscosity at 25° C. from 100, or 300, or 500, or 1,000, or 2,000 to 4,000, or 8,000, or 20,000, or 30,000, or 50,000 mPa.Math.s. In a further embodiment, the polyether polyol has a viscosity at 25° C. from 100 to 50,000, or from 1,000 to 20,000, or from 2,000 to 4,000 mPa.Math.s.

[0047] In an embodiment, the aliphatic polyisocyanate has a density from 0.7, or 0.9, or 1.03, or 1.05, or 1.1, or 1.15 to 1.18, or 1.2, or 1.3, or 1.5, or 1.8 g/cm.sup.3. In a further embodiment, the aromatic polyisocyanate has a density from 0.7 to 1.8 g/cm.sup.3, or from 1.05 to 1.5 g/cm.sup.3, or from 1.1 to 1.2 g/cm.sup.3. In another embodiment, the aromatic polyisocyanate has a density from 1.15 to 1.25 g/cm.sup.3.

[0048] In an embodiment, the aliphatic polyisocyanate has a viscosity at 25° C. from 100, or 300, or 500, or 1,000, or 1,500, or 1,800, or 2,000 to 3,000, or 4,000, or 8,000, or 20,000, or 30,000, or 50,000 mPa.Math.s. In a further embodiment, the polyether polyol has a viscosity at 25° C. from 100 to 50,000, or from 1,000 to 8,000, or from 1,800 to 4,000 mPa.Math.s.

[0049] The polyisocyanate may comprise two or more embodiments disclosed herein.

[0050] The polyol used to form the isocyanate prepolymer is selected from a polyester polyol, a polyether polyol, an aliphatic polyol, and combinations thereof. The polyester polyol, the polyether polyol, and the aliphatic polyol can be any respective polyester polyol, polyether polyol, and aliphatic polyol disclosed herein.

[0051] In an embodiment, the polyol used to form the isocyanate prepolymer includes hydrophobic polyols such as natural oil polyester polyols and modified natural oil polyester polyols. In a further embodiment, the polyol used to form the isocyanate prepolymer includes castor oil and polypropylene-co-ethylene polyol.

[0052] The polyol used to form the isocyanate prepolymer may comprise two or more embodiments disclosed herein.

[0053] In an embodiment, the isocyanate prepolymer is the reaction product of a polyisocyanate, at least one polyol, and an optional catalyst.

[0054] Nonlimiting examples of suitable catalysts include dibutyltin dilaurate, zinc acetate, 2, 2-dimorpholinodiethylether, and combinations thereof.

[0055] In an embodiment, the aromatic isocyanate prepolymer has a density from 0.7, or 0.9, or 1.0, or 1.1, or 1.15 to 1.2, or 1.3, or 1.4, or 1.7, or 1.9 g/cm.sup.3. In a further embodiment, the aromatic isocyanate prepolymer has a density from 0.7 to 1.9 g/cm.sup.3, or from 0.9 to 1.7 g/cm.sup.3, or from 1.1 to 1.3 g/cm.sup.3.

[0056] In an embodiment, the aromatic isocyanate prepolymer has a viscosity at 25° C. from 100, or 250, or 500, or 1,000, or 2,000, or 2,800, or 3,000 to 3,200, or 3,500, or 5,000, or 10,000, or 20,000, or 50,000 mPa.Math.s. In a further embodiment, the aromatic isocyanate prepolymer has a viscosity at 25° C. from 100 to 50,000 mPa.Math.s, or from 250 to 20,000 mPa.Math.s, or from 1,000 to 5,000 mPa.Math.s, or from 2,800 to 3,500 mPa.Math.s, or from 3,000 to 3,200 mPa.Math.s.

[0057] In an embodiment, the aromatic isocyanate prepolymer has a isocyanate content from 0.1, or 1, or 5, or 10, or 13 to 15, or 18, 25, or 40 wt %. In a further embodiment, the aromatic isocyanate prepolymer has a isocyanate content from 0.1 to 40 wt %, or from 1 to 25 wt %, or from 5 to 18 wt %, or from 13 to 15 wt %.

[0058] In an embodiment, the aliphatic isocyanate prepolymer has a density from 0.7, or 0.9, or 1.0, or 1.1, or 1.15 to 1.2, or 1.3, or 1.4, or 1.7, or 1.9 g/cm.sup.3. In a further embodiment, the aliphatic isocyanate prepolymer has a density from 0.7 to 1.9 g/cm.sup.3, or from 0.9 to 1.7 g/cm.sup.3, or from 1.1 to 1.3 g/cm.sup.3.

[0059] In an embodiment, the aliphatic isocyanate prepolymer has a viscosity at 25° C. from 100, or 250, or 500, or 1,000, or 2,000, or 2,800, or 3,200 to 3,700, or 4,000, or 5,000, or 10,000, or 20,000, or 50,000 mPa.Math.s. In a further embodiment, the aliphatic isocyanate prepolymer has a viscosity at 25° C. from 100 to 50,000 mPa.Math.s, or from 250 to 20,000 mPa.Math.s, or from 1,000 to 5,000 mPa.Math.s, or from 2,800 to 4,000 mPa.Math.s, or from 3,200 to 3,700 mPa.Math.s.

[0060] In an embodiment, the aliphatic isocyanate prepolymer has a isocyanate content from 0.1, or 1, or 5, or 10, or 13 to 16, or 20, or 25, or 40 wt %. In a further embodiment, the aliphatic isocyanate prepolymer has a isocyanate content from 0.1 to 40 wt %, or from 1 to 25 wt %, or from 5 to 20 wt %, or from 13 to 16 wt %.

[0061] In an embodiment, the isocyanate component A includes an aromatic isocyanate prepolymer in an amount from 20, or 40, or 60, or 80, or 85 to 90, or 95, or 97, or 99, or 99.5 wt %. In a further embodiment, the isocyanate component A includes an aromatic isocyanate prepolymer in an amount from 20 to 99.5 wt %, or from 60 to 97 wt %, or from 80 to 90 wt %, or from 85 to 90 wt %.

[0062] In an embodiment, the isocyanate component A includes an aliphatic isocyanate prepolymer in an amount from 1, or 3, or 5, or 8, or 10 to 15, or 18, or 20, or 30, or 60 wt %. In a further embodiment, the isocyanate component A includes an aliphatic isocyanate prepolymer in an amount from 1 to 60 wt %, or from 3 to 30 wt %, or from 10 to 20 wt %, or from 10 to 15 wt %.

[0063] Weight percentages are based on a total weight of the isocyanate component A.

[0064] The isocyanate component A may comprise two or more embodiments disclosed herein.

Polyol Component B

[0065] The polyol component B (interchangeably referred to as component B), includes (i) a phosphate-functional polyol, (ii) a polyether polyol, and (iii) an element selected from the group consisting of a polyurethane polyol, a polyester polyol and a combination thereof.

[0066] The phosphate-functional polyol may be represented by structure I:

##STR00001##

[0067] where R.sup.1 is any organic group. In addition to the pendant groups shown in structure I, R.sup.1 may or may not have one or more additional pendant OH groups. Any two or more of the OH groups may or may not be attached to the same atom of R.sub.1. In an embodiment, each OH group is attached to a separate atom of R.sup.1.

[0068] A convenient way to characterize R1 is to describe the compound having structure II:

##STR00002##

[0069] where R.sup.1 is the same as in structure I. The compound having structure II is known herein as a “precursor polyol.”

[0070] In an embodiment, the precursor polyols have molecular weight of 90 or higher; more preferably 200 or higher; more preferably 400 or higher. Preferred precursor polyols have molecular weight of 4,000 or lower; more preferably 2,000 or lower; more preferably 1,200 or lower; more preferably 900 or lower; more preferably 500 or lower.

[0071] In an embodiment, the precursor polyols are alkyl higher polyols, monosaccharides, disaccharides, and compounds having structure III:

##STR00003##

[0072] where each of R.sup.2, R.sup.3, R.sup.4, and R.sup.5 is, independent of the other, any organic group; each of n.sub.1, n.sub.2, and n.sub.3 is, independent of the other, an integer from 0 to 10. In addition to the pendant groups shown in structure III, R.sup.2 may or may not have one or more additional pendant groups. It is further understood that any two or more of the pendant groups may or may not be attached to the same atom of R.sup.2. In some embodiments, a mixture of compounds having structure III is present, where the compounds of structure III differ from each other in the value of one or more of n.sub.1, n.sub.2, and n.sub.3; such mixtures are described herein by stating a non-integer value for the parameter n.sub.1, n.sub.2, or n.sub.3, where the non-integer value represents the number average of that parameter. When it is desired to assess the molecular weight of such a mixture, the number-average molecular weight is used.

[0073] Among precursor polyols having structure III, preferably each pendant group is attached to a separate atom of R.sup.2.

[0074] Among precursor polyols having structure III, preferably, one or more of R.sup.3, R.sup.4, and R.sup.5 is a hydrocarbon group having 1 to 4 carbon atoms; more preferably 2 to 3 carbon atoms; more preferably 3 carbon atoms. Among precursor polyols having structure III, preferably, one or more of R.sup.3, R.sup.4, and R.sup.5 is an alkyl group, which may be linear or cyclic or branched or a combination thereof; more preferably, one or more of R.sup.3, R.sup.4, and R.sup.5 is a linear or branched alkyl group; more preferably, one or more of R.sup.3, R.sup.4, and R.sup.5 is a branched alkyl group. Preferably, R.sup.3, R.sup.4, and R.sup.5 are identical to each other.

[0075] Among precursor polyols having structure III, preferably, one or more of n.sub.1, n.sub.2, and n.sub.3 is from 0 to 8. Among precursor polyols having structure III, preferably, one or more of n.sub.1, n.sub.2, and n.sub.3 is 1 or more. Among precursor polyols having structure III, preferably, one or more of n.sub.1, n.sub.2, and n.sub.3 is 6 or less. Among precursor polyols having structure III, preferably, n.sub.1, n.sub.2, and n.sub.3 are the same as each other.

[0076] In an embodiment, the precursor polyols having structure III are compounds in which each of R.sup.2, R.sup.3, R.sup.4, and R.sup.5 is an alkyl group; such precursor polyols are known herein as alkoxylated alkyl triols. In a triol, when at least one of n.sub.1, n.sub.2, and n.sub.3 is 1 or more and R2 has the structure IV:

##STR00004##

[0077] then the triol is known herein as an alkoxylated glycerol. In alkoxylated triols, when each of R.sup.3, R.sup.4, and R.sup.5 is a branched alkyl group with exactly 3 carbon atoms, the alkoxylated triol is known herein as a propoxylated triol. A propoxylated triol in which R.sup.2 has structure IV is known herein as propoxylated glycerol.

[0078] Among precursor polyols that are alkyl higher polyols, preferred are those with 10 or fewer carbon atoms; more preferred are those with 6 or fewer carbon atoms; more preferred are those with 3 or fewer carbon atoms; more preferred is glycerol.

[0079] More preferred precursor polyols are alkyl higher polyols and compounds having structure III; more preferred are compounds having structure III. It is noted that, if n.sub.1=n.sub.2=n.sub.3=0 and if R.sup.2 is either an alkyl group or an alkyl group having hydroxyl groups, then the compound having structure III is an alkyl higher polyol.

[0080] A preferred group of precursor polyols are alkyl triols and alkoxylated alkyl triols. Among these, more preferred are glycerol and alkoxylated glycerols; more preferred are alkoxylated glycerols. Among alkoxylated glycerols, preferred are propoxylated glycerols.

[0081] Another class of suitable phosphate-functional polyols are those that contain urethane linkages. Preferably, members of this class are made by reacting one or more suitable phosphate-functional polyol with one or more polyisocyanate. The polyisocyanate includes any aromatic polyisocyanate or aliphatic polyisocyanate described herein. In an embodiment, the polyisocyanate of the phosphate-functional polyol is 2,2′-MDI; 2,4′-MDI; 4,4′-MDI; carbodiimide-modified 2,2′-MDI; carbodiimide-modified 2,4′-MDI; carbodiimide-modified 4,4′-MDI; and combinations thereof.

[0082] In an embodiment, the amount of polyisocyanate is kept low enough so that some or all of the reaction products are phosphate-functional polyols. Alternatively, the polyol may be first reacted with the polyisocyanate to make an OH terminated prepolymer which is then reacted with polyphosphoric acid.

[0083] In an embodiment, a method of making the phosphate-functional polyol is to react a precursor polyol with phosphoric-type acid to produce the compound having structure I.

[0084] In an embodiment, the amounts of phosphoric-type acid and precursor polyol are chosen to determine the ratio of Mp:Mx as follows:

[0085] Mhy=number of hydroxyl groups per molecule of the precursor polyol

[0086] Nx=Mhy−2

[0087] Mx=(moles of precursor polyol)×Nx

[0088] Mp=moles of phosphorous atoms contained in the phosphoric-type acid. Preferably, the ratio of Mp:Mx is 0.1:1 or higher; more preferably 0.2:1 or higher; more preferably 0.5:1 or higher; more preferably 0.75:1 or higher. Preferably, the ratio of Mp:Mx is 1.1:1 or less.

[0089] Preferably, the weight ratio of phosphoric-type acid to precursor polyol is 0.005:1 or higher; more preferably 0.01:1 or higher; more preferably 0.02:1 or higher. Preferably, the weight ratio of phosphoric-type acid to precursor polyol is 0.3:1 or lower; more preferably 0.2:1 or lower; more preferably 0.12:1 or lower.

[0090] Preferably, the phosphoric-type acid contains polyphosphoric acid. Preferably, the amount of polyphosphoric acid in the phosphoric-type acid is, by weight based on the weight of the phosphoric-type acid, 75% or more; more preferably 80% or more; more preferably 90% or more. Polyphosphoric acid is available in various grades; each grade is characterized by a percentage. To determine the grade, it is first recognized that pure monomeric orthophosphoric acid, the content of phosphorous pentoxide is considered to be 72.4%. Any grade of polyphosphoric acid can also be analyzed, to consider that one mole of polyphosphoric acid (formula weight labeled “Fppa”) contains the number of moles of phosphorous pentoxide labeled “Nppo,” and the phosphorous pentoxide percentage (“PCppo”) is given by PCppo=(Nppox142)/Fppa, expressed as a percentage. Then, the grade of that polyphosphoric acid is the ratio, expressed as a percentage: Grade=PCppo/72.4.

[0091] Preferably, polyphosphoric acid is used that has grade of 100% or higher; more preferably 110% or higher. Preferably, polyphosphoric acid is used that has grade of 150% or lower; more preferably 125% or lower.

[0092] In an embodiment, the phosphate-functional polyol has a total phosphoric acid content from 0.05%, or 0.1%, or 0.2%, or 0.5% to 1.5%, or 1.8%, or 2% or 3%. In a further embodiment, the phosphate-functional polyol has a total phosphoric acid content from 0.05 to 3%, or from 0.1 to 2%, or from 0.5 to 1.5%.

[0093] In an embodiment, the phosphate-functional polyol has a viscosity at 25° C. from 5,000, or 10,000, or 15,000 to 20,000, or 30,000, or 40,000 mPa.Math.s. In a further embodiment, the phosphate-functional polyol has a viscosity at 25° C. from 5,000 to 40,000 mPa.Math.s, or from 10,000 to 30,000 mPa.Math.s, or from 15,000 to 20,000 mPa.Math.s.

[0094] In an embodiment, the Mn of the phosphate-functional polyol is from 300, or 600, or 900 to 1,100, or 3,000, or 10,000 s. In a further embodiment, the Mn of the phosphate-functional polyol is from 300 to 10,000, or from 600 to 3,000, or from 900 to 1,100.

[0095] In an embodiment, the Mw of the phosphate-functional polyol is from 300, or 800, or 1,500 to 2,000, or 6,000, or 10,000 s. In a further embodiment, the Mw of the phosphate-functional polyol is from 300 to 10,000, or from 800 to 6,000, or from 1,500 to 2,000.

[0096] A nonlimiting example of a suitable phosphate-functional polyol is disclosed in International Publication No. WO 2015/168670, the entire contents of which are incorporated herein.

[0097] The phosphate-functional polyol may comprise two or more embodiments disclosed herein.

[0098] Component B includes a polyether polyol. A “polyether polyol” is a compound that is a polyether and a polyol. Nonlimiting examples of suitable polyether polyols include polyaddition products of ethylene oxide, propylene oxide, tetrahydrofuran, butylene oxide, and the co-addition and grafted products thereof; the polyether polyols obtained by condensation of polyhydric alcohols, or mixtures thereof; and combinations thereof.

[0099] Nonlimiting examples of suitable polyether polyols include polypropylene glycol (PPG), polyethylene glycol (PEG), polybutylene glycol, polytetramethylene ether glycol (PTMEG), and combinations thereof.

[0100] In an embodiment, the polyether polyol has a molecular weight from 50, or 100, or 300, or 400 to 600, or 1,000, or 2,000, or 3,000, or 4,000 or 5,000 g/mol. In a further embodiment, the polyether polyol has a molecular weight from 50 to 4,000, or from 100 to 2,000, or from 400 to 600 g/mol.

[0101] In an embodiment, the polyether polyol has a density from 0.7, or 0.9, or 1.0, or 1.03 to 1.05, or 1.1, or 1.15, or 1.2, or 1.3, or 1.6 g/cm.sup.3. In a further embodiment, the polyether polyol monomer has a density from 0.7 to 1.6 g/cm.sup.3, or from 0.9 to 1.3 g/cm.sup.3, or from 1.0 to 1.1 g/cm.sup.3, or from 1.03 to 1.05 g/cm.sup.3.

[0102] In an embodiment, the polyether polyol has a viscosity at 25° C. from 100, or 300, or 500, or 800, or 1,100 to 1,200, or 1,300, or 2,000 or 8,000, or 20,000, or 50,000 mPa.Math.s. In a further embodiment, the polyether polyol has a viscosity at 25° C. from 100 to 50,000, or from 500 to 8,000, or from 800 to 2,000 or from 1,100 to 1,300 mPa.Math.s.

[0103] In an embodiment, the polyether polyol has a hydroxyl group functionality from 1.5 or 2.0 to 3.0. In a further embodiment, the polyether polyol has a hydroxyl group functionality from 1.5 to 3.0, or from 2.0 to 3.0.

[0104] The polyether polyol of the polyol component B may comprise two or more embodiments disclosed herein.

[0105] In an embodiment, the polyol component B includes a polyurethane polyol. The polyurethane polyol is the reaction product of a polyisocyanate and at least one polyol. The polyisocyanate includes any aromatic polyisocyanate or aliphatic polyisocyanate described herein. The polyol includes any polyol described herein.

[0106] In an embodiment, the polyurethane polyol is a hydroxyl-terminated polyurethane resin.

[0107] In an embodiment, component B includes a polyester polyol. A “polyester polyol” is a compound that is a polyester and a polyol. Nonlimiting examples of suitable polyester polyols include polycondensates of diols, polyols (e.g., triols, tetraols), dicarboxylic acids, polycarboxylic acids (e.g., tricarboxylic acids, tetracarboxylic acids), hydroxycarboxylic acids, lactones, and combinations thereof. The polyester polyols can also be derived from, instead of the free polycarboxylic acids, the corresponding polycarboxylic anhydrides, or corresponding polycarboxylic esters of lower alcohols.

[0108] Nonlimiting examples of suitable diols include ethylene glycol, butylene glycol, diethylene glycol (DEG), triethylene glycol, polyalkylene glycols, such as polyethylene glycol, 1,2-propanediol, 1,3-propanediol, 1,3-butanediol, 1,4-butanediol, 2-methyl-2,4-pentanediol (MPD), 1,6-hexanediol (HDO), neopentyl glycol (NPG), 1,8-octane diol, and combinations thereof. In an embodiment, the diol includes diols having a hydrocarbon backbone containing 12 or more carbon atoms.

[0109] Nonlimiting examples of suitable dicarboxylic acids include aliphatic acids, aromatic acids, and combinations thereof. Nonlimiting examples of suitable aromatic acids include phthalic acid, isophthalic acid, terephthalic acid, and tetrahydrophthalic acid. Nonlimiting examples of suitable of suitable aliphatic acids include hexahydrophthalic acid, hexane dicarboxylic acid, cyclohexane dicarboxylic acid, octane dicarboxylic acid, dodecane dicarboxylic acid, adipic acid, azelaic acid, sebacic acid, glutaric acid, tetrachlorophthalic acid, maleic acid, fumaric acid, itaconic acid, malonic acid, suberic acid, 2-methyl succinic acid, 3, 3-diethyl glutaric acid, 2, 2-dimethyl succinic acid, and trimellitic acid. As used herein, the term “acid” also includes any anhydrides of said acid. Saturated aliphatic and/or aromatic acids are also suitable, such as adipic acid or isophthalic acid.

[0110] In an embodiment, monocarboxylic acids, such as benzoic acid and hexane carboxylic acid, are excluded from the solventless adhesive composition.

[0111] In an embodiment, the polyester polyol is a natural oil polyol or the transesterification reaction product of natural oil polyol and a polyester polyol. The polyester polyol suitable for use in the transesterification reaction includes any polyester polyol described herein.

[0112] In an embodiment, the polyester polyol is castor oil. In a further embodiment, the polyester polyol is the transesterification reaction product of castor oil and a polyester polyol.

[0113] In an embodiment, the polyester polyol has a molecular weight from 500 g/mol to 2,000 g/mol, or 3,000 g/mol, or 4,000 g/mol. In a further embodiment, the polyester polyol has a molecular weight from 500 g/mol to 2,000 g/mol.

[0114] In an embodiment, the polyester polyol has a density from 0.7, or 0.9, or 1.0, or 1.03 to 1.05, or 1.1, or 1.15, or 1.2, or 1.3, or 1.6 g/cm.sup.3. In a further embodiment, the aromatic polyisocyanate has a density from 0.7 to 1.6 g/cm.sup.3, or from 0.9 to 1.3 g/cm.sup.3, or from 1.0 to 1.1 g/cm.sup.3, or from 1.03 to 1.05 g/cm.sup.3.

[0115] In an embodiment, the polyester polyol has a viscosity at 25° C. from 100, or 300, or 500, or 800, or 900 to 1,000, or 1,200, or 2,000 or 8,000, or 20,000, or 50,000 mPa.Math.s. In a further embodiment, the polyether polyol has a viscosity at 25° C. from 100 to 50,000, or from 500 to 8,000, or from 800 to 1,200, or from 900 to 1,000 mPa.Math.s.

[0116] In an embodiment, the polyester polyol has a hydroxyl group functionality from 1.5, or 2.0 to 3.0. In a further embodiment, the polyester polyol has a hydroxyl group functionality from 1.5 to 3.0, or from 2.0 to 3.0. To achieve hydroxyl group functionality greater than 2, polyols having a hydroxyl group functionality of 3 or more (e.g., trimethylolpropane (TMP), glycerol, erythritol, pentaerythritol, trimethylolbenzene, and/or trishydroxyethyl isocyanurate) may be included in the polyester polyol.

[0117] The polyester polyol may comprise two or more embodiments disclosed herein.

[0118] In an embodiment, component B has from 0.5 wt %, or 1 wt %, or 3 wt %, or 6 wt %, or 8 wt %, or 10 wt % to 12 wt %, or 14 wt %, or 16 wt %, or 25 wt %, or 50 wt % phosphate-functional polyol. In another embodiment, component B has from 0.5 to 50 wt %, or from 1 wt % to 50 wt %, or from 6 wt % to 16 wt %, or from 10 wt % to 12 wt % phosphate-functional polyol.

[0119] In an embodiment, component B has from 5 wt %, or 10 wt %, or 20 wt % to 60 wt %, or 80 wt %, or 90 wt % polyether polyol. In another embodiment, component B has from 5 wt % to 90 wt %, or from 10 wt % to 80 wt %, or from 20 wt % to 60 wt % polyether polyol.

[0120] In an embodiment, component B has from 0.05 wt %, or 0.1 wt %, or 0.5 wt %, or 1 wt % to 50 wt %, or 60 wt %, or 70 wt %, or 80 wt % polyester polyol. In another embodiment, component B has from 0.05 wt % to 80 wt %, or from 0.5 wt % to 70 wt %, or from 1 wt % to 50 wt % polyester polyol.

[0121] In an embodiment, component B has from 5 wt %, or 10 wt %, or 20 wt %, or 30 wt % to 40 wt %, or 50 wt % to 60 wt % to 70 wt %, or 80 wt %, or 90 wt % polyurethane polyol. In another embodiment, component B has from 10 wt % to 90 wt %, or from 20 wt % to 80 wt %, or from 20 wt % to 60 wt %, from 20 wt % to 40 wt % polyurethane polyol.

[0122] In an embodiment, component B has from 1 to 50 wt %, or from 8 to 14 wt %, or from 10 to 12 wt % of the phosphate-functional polyol and from 60 to 99 wt %, or from 85 to 95 wt %, or from 88 to 92 wt % of the polyether polyol.

[0123] In an embodiment, component B has from 1 to 50 wt %, or from 8 to 14 wt %, or from 10 to 12 wt % of the phosphate-functional polyol and from 60 to 90 wt %, or from 87 to 98 wt %, or from 90 to 96 wt % of the polyester polyol.

[0124] Weight percentages are based upon the total weight of the polyol component B.

[0125] The polyol component B may comprise two or more embodiments disclosed herein.

[0126] It is understood that the sum of the weights of the compounds (polyisocyanates, polyols) in any component disclosed herein (e.g., component A) is 100 percent, based on a total weight of the respective component.

C. Mixing (A) and (B) to Form an SLA Composition

[0127] The process includes mixing an isocyanate component (A) and a polyol component (B) to form a solventless adhesive (SLA) composition.

[0128] A “solventless adhesive” composition is an adhesive composition that is void of, or substantially void of, a solvent.

[0129] It is contemplated that component A and component B can be formed separately and, if desired, stored until it is desired to use the SLA composition. When it is desired to use the SLA composition, component A and component B are brought into contact with each other and mixed together. It is contemplated that when the two components are brought into contact, a curing reaction begins in which the isocyanate groups react with hydroxyl groups to form urethane linkages. The SLA composition formed by bringing the two components into contact is termed a “curable mixture.”

[0130] In an embodiment, component A and component B is each a liquid at 25° C.

[0131] In an embodiment, component A is heated to and maintained at a temperature from 25° C., or 40° C., or 45° C., or 50° C. to 55° C., or 65° C., or 70° C. or 80° C.; component B is heated to and maintained at a temperature from 25° C., or 40° C., or 45° C., or 50° C. to 55° C., or 65° C., or 70° C. or 80° C.; and component A and component B are brought into contact with each other and mixed. In a further embodiment, component A is heated to and maintained at a temperature from 30° C. to 60° C., or from 35° C.5 to 55° C.; component B is heated to and maintained at a temperature from 25° C. to 80° C., or from 30° C. to 55° C.; and component A and component B are brought into contact with each other and mixed.

[0132] Component A and component B are mixed with any means suitable for forming the composition as described herein. In an embodiment, component A and component B are mixed with a high speed mixer or a continuous mixing nozzle.

[0133] In an embodiment, the SLA composition has a weight ratio of component A to component B from 100:400, or 100:200, or 100:150, or 100:100, or 100:95, or 100:91, or 100:90, or 100:87, or 100:85, or 100:83, or 100:82, or 100:80 to 100:70, or 100:68, or 100:66, or 100:64, or 100:60, or 100:50, or 100:30, or 100:20, or 100:10, or 100:5. In a further embodiment, the SLA composition has a weight ratio of component A to component B from 1:4 to 20:1, or from 10:9 to 10:3, or from 100:85 to 100:64, or from 100:80 to 100:70.

[0134] In an embodiment, the SLA composition has the phosphate-functional polyol present in an amount from 0.1, or 1, or 4 to 7, or 20 or 40 wt %. In a further embodiment, the SLA composition has the phosphate-functional polyol present in an amount from 0.1 to 40 wt %, or from 1 to 20 wt %, or from 4 to 7 wt %. Weight percentage of the phosphate-functional polyol is based on a total weight of the SLA composition (i.e., the sum of the weights of component A and component B).

[0135] The SLA composition has a pot life. The pot life is measured from the time the SLA composition is formed. In an embodiment, the pot life is from 20 min, or 30 min, or 35 min, or 40 min to 50 min, or 60 min, or 70 min, or 90 min, or 200 min at 40° C. In a further embodiment, the pot life is from 20 to 200 min, or from 35 to 90 min, or from 35 to 70 min, or from 40 to 60 min at 40° C. The pot life is measured in accordance with the pot life test described herein.

[0136] The SLA composition has a primary aromatic amine (PAA) decay level. The PAA decay level is reported in parts per billion (ppb). In an embodiment, the PAA decay level is from 0.01 ppb, or 0.1 ppb, or 0.5 ppb, to 1.0, or 1.4, or 1.9 ppb. In a further embodiment, the PAA decay level is from 0.01 to 1.9 ppb, or from 0.1 ppb to 1.4 ppb, or from 0.5 to 1.4 ppb, or from 0.5 to 1 ppb. In another embodiment, the PAA decay level is measured after 24 hours curing at 25° C. and 50% humidity and in accordance with the PAA decay test described herein.

D. Applying the SLA Composition

[0137] The process includes applying the SLA composition between a first film and a second film to form a raw laminate. In an embodiment, the SLA composition is applied onto the first film that is then laminated with the second film to form the raw laminate. Nonlimiting examples of suitable methods of applying the SLA composition include brushing, pouring, spraying, coating, rolling, spreading, and injecting.

[0138] In an embodiment, the SLA composition is applied with the use of the laminator. Nonlimiting examples of laminators suitable for use to apply the SLA composition include a Labcombi pilot machine coater and a Nordmeccanica Super Combi 3000 laminator. In an embodiment, the laminator is a non-mechanical super simplex laminator. A non-mechanical super simplex laminator applies a pre-mixed SLA composition on the first film that is laminated onto the second film by (i) metering of each component (the polyol component and the isocyanate component), (ii) mixing the isocyanate component A and the polyol component B, and (iii) dispensing the mixture onto the first film.

[0139] The SLA composition is applied between the first film and the second film at a temperature from 35° C., or 40° C., or 45° C. to 50° C., or 55° C., or 60° C., or 70° C. or 80° C., or 85° C. In an embodiment, the SLA composition is applied between the first film and the second film at a temperature from 35° C. to 55° C.

[0140] In an embodiment, the SLA composition is applied at a coating weight from 1 g/m.sup.2, or 1.1 g/m.sup.2, or 1.2 g/m.sup.2, or 1.5 g/m.sup.2, or 2 g/m.sup.2 to 3 g/m.sup.2, or 4 g/m.sup.2, or 5 g/m.sup.2, or 8 g/m.sup.2, or 15 g/m.sup.2. In a further embodiment, the SLA composition is applied at a coating weight from 1 to 15 g/m.sup.2, or from 1.2 to 5 g/m.sup.2, or from 1.5 to 3 g/m.sup.2. In another embodiment, the SLA composition is applied at a coating weight from 1 to 1.2 g/m.sup.2, or from 1 to 1.1 g/m.sup.2. Not wishing to be bound by any particular theory, it is believed that the use of a SLA composition enables a lower coating weight, or coating weight from 1.2 to 5 g/m.sup.2, or from 1.5 to 3 g/m.sup.2 compared to conventional solvent-based adhesives. A lower coating weight is advantageous to reduce costs, to reduce the weight of the adhesive applied to the film layers, and to reduce the weight of the laminate product.

[0141] The process of applying the SLA composition may comprise two or more embodiments disclosed herein.

[0142] The process includes the step of curing the raw laminate to form the laminate product. The raw laminate product is cured at a temperature from 20° C., or 25° C., or 30° C. to 35° C., or 40° C., or 50° C. for a period of time from 4 hours (h), or 8 h, or 12 h to 18 h, or 24 h, or 36 h, or 48 h, or 72 h. In an embodiment, the raw laminate is cured at a temperature from 20° C. to 35° C. for a period of time from 6 h to 72 h, or from 12 h to 36 h, or from 20 h to 28 h.

[0143] In an embodiment, curing is complete after holding the raw laminate at a temperature from 20° C. to 25° C. for 24 h.

[0144] In an embodiment, curing the raw laminate includes drying the raw laminate. In a further embodiment, curing the raw laminate excludes passing the raw laminate through an oven.

[0145] The process of the present disclosure may comprise two or more embodiments disclosed herein.

E. Laminate Product

[0146] The present disclosure provides a laminate product.

[0147] In an embodiment, the laminate product is a multilayer film. In a further embodiment, the laminate product is a pouch. In an embodiment, the pouch is used for packaging food products.

[0148] The laminate product includes a first film, a second film, and a solventless adhesive (SLA) composition disposed between the first film and the second film. The SLA composition of the laminate product is any SLA composition described herein.

[0149] In an embodiment, the first film and the second film are independently selected from the group consisting of metallized films, aluminum foils, polymer films, ink-printed films, coated films, co-extruded films, polyethylene (PE) films, polyethylene terephthalate (PET) films, polyester films, polyolefin based films, polyamide based films, copolymer films and paper.

[0150] In an embodiment, the composition of the first film is the same as the composition of the second film. In a further embodiment, the composition of the first film is different than the composition of the second film.

[0151] Each film has a thickness from 5 μm, or 12 μm, or 20 μm to 40 μm, or 70 μm, or 200 μm, or 300 μm. In another embodiment, each film has a thickness from 5 to 300 μm, or from 12 to 70 μm, or from 20 μm to 40 μm. Each film may have the same thickness or a different thickness than the other film. In an embodiment, each film has the same thickness.

[0152] The laminate product may comprise two or more embodiments disclosed herein.

[0153] In an embodiment, the bond strength of the laminate product is measured after the laminate product is exposed to conditions of elevated pressure and temperature as described in the anti-seal test.

[0154] In an embodiment, the laminate product includes 48 g PET film and white PE film and has a bond strength from 3,415 to 4,000 g/25 mm after being exposed to conditions of elevated pressure and temperature as described in the anti-seal test. In an embodiment, the laminate product includes 48 g PET film and white PE film and has a bond strength from 3,580 to 4,200 g/25 mm after being exposed to conditions of elevated pressure and temperature as described in the anti-seal test. In an embodiment, the laminate product includes 48 g PET film and white PE film and has a bond strength from 2,680 to 3,550 g/25 mm after being exposed to conditions of elevated pressure and temperature as described in the anti-seal test. In an embodiment, the laminate product includes 48 g PET film and white PE film and has a bond strength from 1,650 to 3,030 g/25 mm after being exposed to conditions of elevated pressure and temperature as described in the anti-seal test.

[0155] The bond strength after the anti-seal test can be termed an anti-seal value. In an embodiment, the anti-seal value of the laminate product is from 2 to 12 times more than the anti-seal value of a laminate product formed with a solventless adhesive composition not comprising a phosphate-functional polyol.

[0156] In an embodiment, the bond strength of the laminate product is measured after the laminate product is exposed to an aging food simulant as described in the food resistance test. In an embodiment, the bond strength of the laminate product is measured after the laminate product is exposed to a boiling food simulant as described in the rigorous food resistance test. The bond strength obtained after the food resistance test or after the rigorous food resistance test is measured in accordance with the bond strength test.

[0157] In an embodiment, the laminate product includes 48 g PET film and PE film and has a bond strength from 510 to 725 g/25 mm after being exposed to an aging food simulant. In an embodiment, the laminate product includes 48 g PET film and PE film and has a bond strength from 600 to 850 g/25 mm after being exposed to a boiling food simulant.

[0158] In an embodiment, the laminate product includes 48 g PET film and white PE film and has a bond strength from 390 to 760 g/25 mm after being exposed to an aging food simulant. In an embodiment, the laminate product includes 48 g PET film and white PE film and has a bond strength from 830 to 900 g/25 mm after being exposed to a boiling food simulant.

[0159] In an embodiment, the laminate product includes metallized film and PE film and has a bond strength from 140 to 400 g/25 mm after being exposed to an aging food simulant. In an embodiment, the laminate product includes metallized film and PE film and has a bond strength from 900 to 1020 g/25 mm after being exposed to a boiling food simulant.

[0160] The bond strength after the food resistance test or the rigorous food resistance test can be termed a food resistance value. In an embodiment, the food resistance value of the laminate product is from 200 to 400 percent more than the food resistance value of a laminate product formed with a solventless adhesive composition not comprising a phosphate-functional polyol.

[0161] In an embodiment, the PAA decay level of the laminate product is from 180 to 220 percent less than the PAA decay level of a laminate product formed with a solventless adhesive composition not comprising a phosphate-functional polyol.

[0162] In an embodiment, the outgassing rating of the laminate product is from 300 to 500 percent more than the outgassing rating of a laminate product formed with a solventless adhesive composition not comprising a phosphate-functional polyol.

[0163] By way of example, and not limitation, some embodiments of the present disclosure will now be described in detail in the following examples.

EXAMPLES

[0164] The raw materials for use in the Inventive Examples (“IE”) and Comparative Samples (“CS”) are detailed in Table 1 below.

TABLE-US-00001 TABLE 1 Commercial Name Composition/properties Source Component A PACACEL ™ Aromatic isocyanate MDI-based The Dow L75-191 Density: 1.11-1.15 g/cm.sup.3 Chemical Viscosity: 2,000-4,000 mPa .Math. s@25° C. Company MOR-FREE ™ Aliphatic isocyanate HDI trimer The Dow C-33 Density: 1.1-1.2 g/cm.sup.3 Chemical Viscosity: 1800-4000 mPa .Math. s@25° C. Company Adcote ™ Solvent-based isocyanate The Dow 577 Density: 1.14-1.18 g/cm.sup.3 Chemical Viscosity: 3800-4000 mPa .Math. s@25° C. Company Solid content: 75% Component B Coreactant I Blend of propylene-based polyether polyol, polyurethane polyol, and 2 wt % phosphate-functional polyol Density: 1.0-1.1 g/cm.sup.3 Viscosity: 1100-1300 mPa .Math. s @ 25° C. Coreactant II Blend of polyester polyol, polyether polyol, and 8% phosphate-functional polyol Density: 1.0-1.1 g/cm.sup.3 Viscosity: 800-1200 mPa .Math. s @ 25° C. Phosphate- Phosphoric acid content: 0.5 to 3 wt % The Dow functional Viscosity: 5,000-40,000 mPa .Math. s @ 25° C. Chemical polyol Mn: 900 to 1,100; Mw: 1,500 to 2,000 Company Adcote ™ Solvent-based polyol The Dow L87-124 Density 1.03-1.05 g/cm3 Chemical Viscosity: 900-1000 mPa .Math. s @ 25° C. Company Solid content: 89% CR-85 Solventless polyol blend The Dow Density: 0.99-1.02 g/cm.sup.3 Chemical Viscosity: 600-800 mPa .Math. s @ 25° C. Company

[0165] Solventless adhesive (SLA) compositions for Inventive Examples IE 1, IE 2, IE 3 and Comparative Samples CS 1, CS 2, CS 3 are prepared according to the formulations listed in Table 2 using the raw materials listed in Table 1.

[0166] The SLA compositions are used to prepare laminates from film substrates. The SLA compositions are applied onto a first film that is laminated to a second film to form the laminate product. The first film is selected from either (i) 48-gauge polyethylene terephthalate (PET) or (ii) aluminum foil. The second film is selected from either (i) polyethylene (PE) or (ii) white pigmented PE. Lamination is conducted using a LABO COMBI pilot machine coater. Temperature of SLA composition is 40° C. Temperature of machine coater nip is 40° C.

[0167] The films are laminated at 100 meters per minute with the coating weights listed in Table 2.

[0168] A solvent-based adhesive was used for Comparative Sample 3 (CE 3).

[0169] The laminates are cured at 25° C. and 50% humidity for 7 days.

[0170] The performance results are summarized at the bottom of Table 2.

TABLE-US-00002 TABLE 2 Component CS1 CS2 CS3 IE2 IE3 IE1 Weight Percentages based on component A PACACEL ™ L75-191 100 87.5 87.5 87.5 87.5 C-33 12.5 12.5 12.5 12.5 Adcote ™ 577 100 Weight Percentages based on component B Coreactant I 100 90 Coreactant II 93 100 Phosphate-functional polyol 10 7 Adcote ™ L87-124 100 CR-85 100 Phosphate-functional polyol 12 14 8 in Component B (wt %) Solentless Adhesive Composition A/B weight-to-weight ratio 100/60 100/50 100/7 100/64 100/82 100/85 Phosphate-functional polyol 5 7 4 in SLA composition (wt %) Coating weight (g/m.sup.2) 1.8 1.7 4.1 1.8 1.7 1.8 Performance Pot life (min) 60 38 38 41 49 PAA Decay (ppb) 1.483 0.847 0.762 0.621 Outgassing Rating 1 1 3 4 5 Food Resistance for 48 g PET//PE [Bond Strength (g/25 mm)] Rigorous 143 228 483 593 600 843 Aging 250 183 383 560 718 505 Food Resistance for 48 g PET//white PE [Bond Strength (g/25 mm)] Rigorous 575 550 893 828 848 Aging 348 313 688 750 380 Food Resistance for Al foil//PE [Bond Strength (g/25 mm)] Rigorous 298 268 808 1010 893 988 Aging 15 13 330 138 385 283 Anti-Seal for 48 g PET//white PE [Bond Strength (g/25 mm)] 104.4° C. 10 15 18 18 30 115.5° C. 30 80 148 315 360 126.7° C. 1280 1463 1640 3013 2893 137.8° C. 1213 2400 2663 3503 3360 148.8° C. 1398 2853 3560 3768 4153 160.0° C. 1403 2798 3413 3630 3958 Curing Time (h) Cleaning Ability (Number of Rub Cycles) 5 10 40 10 20 10 8 (run 1) 35 118 10 110 35 8 (run 2) 45 123 10 115 50

[0171] Applicant unexpectedly discovered that laminates formed between matched films using a solventless adhesive composition containing a phosphate-functional polyol exhibit bond strength from 593 g/25 mm to 1010 g/25 mm after a rigorous food resistance test and bond strength from 3413 g/25 mm to 3958 g/25 mm after an anti-seal test at 160° C. Laminates formed between aluminum foil and polyethylene exhibit bond strength from 893 g/25 mm to 1010 g/25 mm after a rigorous food resistance test.

[0172] Laminates formed between matched films using a solventless adhesive composition containing a phosphate-functional polyol exhibit a pot life from 38 min to 49 min; a primary aromatic amine decay level from 0.621 ppb to 0.847 ppb; and an outgassing rating from 3 to 5.

[0173] It is specifically intended that the present disclosure not be limited to the embodiments and illustrations contained herein, but include modified forms of those embodiments including portions of the embodiments and combinations of elements of different embodiments as come with the scope of the following claims.