High-solids content solvent-based adhesive compositions and methods of making same

Patent metadata

Field	Value
Publication number	US-11220617-B2
Application number	US-201716316926-A
Country	US
Kind code	B2
Filing date	May 22, 2017
Priority date	Jul 11, 2016
Publication date	Jan 11, 2022
Grant date	Jan 11, 2022

Abstract

A two-component adhesive composition is disclosed. The adhesive composition comprises an isocyanate component comprising an isocyanate-terminated prepolymer that is the reaction product of a polyisocyanate and an isocyanate reactive component having an average molecular weight less than 1,500. The NCO content of the isocyanate component without solvent is between 9 and 18%. The composition further comprises a polyol component comprising a polyester polyol having a molecular weight greater than 1,500 that is the reaction product of a polyhydric alcohol and a polybasic acid. The composition still further comprises an adhesion promoter. The average functionality of the adhesive composition is from 2 to 2.4. The adhesive composition provides for improved performance and processability at a solid content greater than 45 wt %. A methods of forming the adhesive composition is also disclosed. A laminate formed by this method is also disclosed.

First claim

The invention claimed is:

1. A two-component adhesive composition, comprising:
an isocyanate component comprising an isocyanate prepolymer that is the reaction product of:
a polyisocyanate; and
an isocyanate reactive component having an average molecular weight less than 1,500, comprising a polyester polyol and a polyether polyol, wherein the polyether polyol comprises at least 50 wt % of the isocyanate reactive component;

a polyol component comprising a polyester polyol having an average molecular weight greater than 1,500, wherein the polyester polyol comprises at least 30 wt % of the polyol component, based on the dry weight of the polyol component, and the polyol component further comprises one or more low molecular weight glycols selected from ethylene glycol, diethylene glycol, triethylene glycol, propylene glycol, trimethylene glycol, 1,3-butanediol, 1,4-butanediol, 1,6-hexanediol, trimethylolpropane, triisopropanolamine, and neopentylglycol; and
an adhesion promoter,
wherein the average functionality of the adhesive composition is greater than 2 but less than 2.41 wherein the adhesive composition further comprises a solvent.

2. The composition of claim 1 , further comprising an initial viscosity at room temperature from 10 seconds to 22 seconds when mixed at a NCO/OH index from 1.0:1.0 to 2.5:1.0 to form a solution with a solids content at 50%.

3. The composition of claim 1 , wherein the polyester polyols are the reaction product of polyhydric alcohols and polybasic acids.

4. The composition of claim 1 , wherein the NCO content of the isocyanate component without solvent is from 9 to 18%.

5. The composition of claim 1 , wherein the NCO content of the isocyanate component without solvent is from 11 to 15%.

6. The composition of claim 1 , wherein the isocyanate reactive component has an average molecular weight from 250 to 1,200.

7. The composition of claim 1 , further comprising an additive selected from the group consisting of a catalyst, a surfactant, a leveling agent, a defoamer, a rheology modifier, a color pigment, and mixtures of two or more thereof.

8. The composition of claim 1 , wherein the solvent is selected from the group consisting of ethyl acetate, methyl ether ketone, toluene, and mixture of two or more thereof.

9. The composition of claim 1 , wherein the isocyanate component further comprises a polyisocyanate selected from the group consisting of aromatic polyisocyanates, aliphatic polyisocyanates, cycloaliphatic polyisocyanates, and mixtures of two or more thereof.

10. The composition of claim 1 , wherein the polyisocyanate is selected from the group consisting of 1,3- and 1,4-phenylene diisocyanate, 1,5-naphthylene diisocyanate, 2,6-tolulene diisocyanate (2.6-TDI), 2,4-tolulene diisocyanate (2,4-TDI), 2,4′-diphenylmethane diisocyanate (2,4′-MDI), 4,4′-diphenylmethane diisocyanate (4,4′-MDI), polymeric isocyanates, 3,3′-Dimethyl-4,4′-Biphenyldiisocyanate (TODI), and combinations of two or more thereof.

11. The composition of claim 1 , wherein the polyisocyanate is selected from the group consisting of cyclohexane diisocyanate, methylcyclohexane diisocyanate, ethylcyclohexane diisocyanate, propylcyclohexane diisocyanate, methyldiethylcyclohexane diisocyanate, propane diisocyanate, butane diisocyanate, pentane diisocyanate, hexane diisocyanate, heptane diisocyanate, octane diisocyanate, nonane diisocyanate, nonane triisocyanate, such as 4-isocyanatomethyl-1,8-octane diisocyanate (TIN), decane di- and triisocyanate, undecane di- and triisocyanate and dodecane di- and triisocyanate, isophorone diisocyanate (IPDI), hexamethylene diisocyanate (HDI), diisocyanatodicyclohexylmethane (H12MDI), 2-methylpentane diisocyanate (MPDI), 2,2,4-trimethylhexamethylene diisocyanate/2,4,4-trimethylhexamethylene diisocyanate (TMDI), norbornane diisocyanate (NBDI), xylylene diisocyanate (XDI), tetramethylxylylene diisocyanate, and dimers, trimers, and combinations of two or more thereof.

12. The composition of claim 1 , wherein the polyisocyanate is selected from the group consisting of 4-methyl-cyclohexane 1,3-diisocyanate, 2-butyl-2-ethylpentamethylene diisocyanate, 3(4)-isocyanatomethyl-1-methylcyclohexyl isocyanate, 2-isocyanatopropylcyclohexyl isocyanate, 2,4′-methylenebis(cyclohexyl) diisocyanate, 1,4-diisocyanato-4-methyl-pentane, and combinations of two or more thereof.

13. The composition of claim 1 , wherein the adhesion promoter is selected from phosphoric acid, polyphosphoric acid, phosphate ester, silane, and mixtures of two or more thereof.

14. The composition of claim 3 , wherein the polyhydric alcohol is selected from the group consisting of a glycol, a polyester, a polyether, and mixtures of two or more thereof.

15. The composition of claim 3 , wherein the polybasic acid is selected from the group consisting of polycarboxylic acid, polycarboxylic anhydride, isophthalic acid, terephthalic acid, and mixtures of two or more thereof.

16. A method for making a laminate structure comprising the adhesive composition of any of claim 1 , the method comprising:
mixing the isocyanate component and the polyol component at a stoichiometric ratio (NCO/OH) from 1 to 2.5 to form a curable adhesive mixture;
dissolving the curable adhesive mixture in a solvent to form a coatable adhesive mixture;
coating the coatable adhesive mixture on a surface of a first substrate;
bringing a surface of a second substrate into contact with the surface of the first substrate under pressure to form a laminate structure; and
curing the laminate structure.

17. A laminate formed by the method of claim 16 .

Assignees

• Dow Global Technologies Llc

Inventors

• Xie Rui
• Gelfer Mikhail Y
• Barrus Jonathan

Classifications

• C08G18/8029

  Masked aromatic polyisocyanates · CPC title

• C08G18/00

  Polymeric products of isocyanates or isothiocyanates · CPC title

• C08G18/7671

  containing only one alkylene bisphenyl group · CPC title

• C08G18/4211

  derived from aromatic dicarboxylic acids and dialcohols · CPC title

• C09J175/04

  Polyurethanes · CPC title