Adhesive-forming composition and blend of adhesives obtained therefrom

• US 7,829,116 B2
• Filed: 11/14/2006
• Issued: 11/09/2010
• Est. Priority Date: 11/14/2006
• Status: Active Grant

• Current Assignee: Momentive Performance Materials Incorporated (Momentive Performance Materials Holdings LLC)
• Original Assignee: Momentive Performance Materials Incorporated (Momentive Performance Materials Holdings LLC)
• Inventors: Bisaillon, Mark J., Frye, Robert L., Griswold, Roy M.
• Primary Examiner(s): Zimmer; Marc S
• Application Number:
  US11/598,925
• Publication Number:
  US 20080114098A1
• Time in Patent Office: 1,456 Days
• Field of Search: 524/55
• US Class Current: 424/484
• CPC Class Codes: A61K 9/7069 obtained otherwise than by reactions only involving carbon to carbon unsaturated bonds, e.g. polysiloxane, polyesters, polyurethane, polyethylene oxide
• CPC Class Codes: C08G 18/12 using two or more compounds having active hydrogen in the first polymerisation step
• CPC Class Codes: C08G 18/4202 Two or more polyesters of different physical or chemical nature C08G18/44 takes precedence
• CPC Class Codes: C08G 18/4236 containing only aliphatic groups
• CPC Class Codes: C08G 18/69 Polymers of conjugated dienes hydrogenated polymers of conjugated dienes C08G18/6208
• CPC Class Codes: C08G 18/718 containing silicon
• CPC Class Codes: C08G 18/755 and at least one isocyanate or isothiocyanate group linked to a secondary carbon atom of the cycloaliphatic ring, e.g. isophorone diisocyanate
• CPC Class Codes: C08G 2170/40 Compositions for pressure-sensitive adhesives
• CPC Class Codes: C08L 83/00 Compositions of macromolecular compounds obtained by reactions forming in the main chain of the macromolecule a linkage containing silicon with or without sulfur, nitrogen, oxygen or carbon only; Compositions of derivatives of such polymers
• CPC Class Codes: C09J 175/04 Polyurethanes

Abstract

The present invention relates to novel adhesive-forming compositions of silylated polyurethane prepolymer blended with pre-formed adhesives, and pressure sensitive adhesives containing the same. The silylated polyurethane prepolymer is obtained from the silylation of a polyurethane prepolymer derived from the reaction of polybutadiene polyol and polyisocyanante, where the polybutadiene polyol possesses a primary hydroxyl group content of from about 0.1 to about 2.0 meq/g.

Claims

1. An adhesive-forming composition comprising:

a) adhesive-forming, moisture-curable silylated polyurethane prepolymer, the silylated polyurethane prepolymer being obtained from the silylation of a polyurethane prepolymer derived from the reaction of polybutadiene polyol and polyisocyanate, wherein the polybutadiene polyol possesses a number average molecular weight of from about 500 to about 10,000 and possesses a primary hydroxyl group content of from about 0.1 to about 2.0 meq/g; and

,

b) adhesive other than the adhesive-forming, moisture-curable silylated polyurethane prepolymer (a), wherein the adhesive is selected from the group consisting of polyurethane adhesives, acrylic adhesives, silicone adhesives, and combinations thereof.

2. The adhesive-forming composition of claim 1 further comprising at least one catalyst for the polyurethane prepolymer reaction.

3. The adhesive-forming composition of claim 1 wherein the polybutadiene polyol possesses a number average molecular weight of from about 800 to about 5,000.

4. The adhesive-forming composition of claim 1 wherein the polyurethane prepolymer is silylated with at least one compound selected from the group consisting of aminosilane and isocyanatosilane.

5. The adhesive-forming composition of claim 4 wherein the aminosilane is of the general formula:

6. The adhesive-forming composition of claim 5 wherein the aminosilane is selected from the group consisting of 3-aminopropyltrimethoxysilane, 3-aminopropylthethoxysilane, 4-aminobutyltriethoxy-silane, N-methyl-3-amino-2-methylpropyltrimethoxysilane, N-ethyl-3-amino-2-methylpropyltrimethoxysilane, N-ethyl-3-amino-2-methylpropyldiethoxymethylsilane, N-ethyl-3-amino-2-methylpropyltriethoxysilane, N-ethyl-3-amino-2-methylpropyl-methyldimethoxysilane, N-butyl-3-amino-2-methylpropyltrimethoxysilane, 3-(N-methyl-2-amino-1-methyl-1-ethoxy)-propyltrimethoxysilane, N-ethyl-4-amino-3,3-dimethyl-butyldimethoxymethylsilane, N-ethyl-4-amino-3,3-dimethylbutyltrimethoxy-silane, N-(cyclohexyl)-3-aminopropyltrimethoxysilane, N-(2-aminoethyl)-3-aminopropyltrimethoxysilane, N-(2-aminoethyl)-3-aminopropyltriethoxy-silane, N-(2-aminoethyl)-3-aminopropylmethyldimethoxysilane, aminopropyltriethoxysilane, bis-(3-trimethoxysilyl-2-methylpropyl)amine and N-(3′

-trimethoxysilylpropyl)-3-amino-2-methylpropyltrimethoxysilane and mixtures thereof, and wherein the isocyanatosilane is selected from the group consisting of λ

-isocyanatopropyltrimethoxysilane, λ

-isocyanatopropyltriethoxy-silane, λ

-isocyanatomethylpropyltrimethoxysilane, λ

-isocyanatomethylpropyltriethoxysilane, λ

-isocyanatopropylmethyldimethoxysilane, λ

-isocyanatopropyldimethylmethoxysilane and λ

-isocyanatomethylpropyldimethylmethoxysilane, and mixtures thereof.

7. The adhesive-forming composition of claim 1 wherein component (b) is moisture-curable silylated polyurethane resin.

8. The adhesive-forming composition claim 1 further comprising at least one additional component selected from the group consisting of filler, tackifier, silane adhesion promoter, plasticizer, solvent, thixotropic agent, U.V. stabilizer, antioxidant and curing catalyst.

9. The adhesive-forming composition of claim 8 wherein the tackifier is MQ tackifier resin containing curing catalyst therefor.

10. An adhesive composition resulting from the moisture-curing of the adhesive-forming composition of claim 1.

11. The adhesive composition of claim 10 further comprising a therapeutically effective amount of drug.

12. The adhesive composition of claim 11 wherein the drug is at least one member selected from the group consisting of penicillins, cephalosporins, erythromycins, tetracyclines, macrolides, aminoglycosides, fosfomycins, rifampicins, mefenamic acid, flufenamic acid, indometacin, diclofenac, acetaminophen, alclofenac, oxyphenbutazone, phenylbutazone, ibuprofen, ketoprofen, salicylic acid, methyl salicylate, L-menthol, camphor, sulindac, naproxen, fenbufen, aspirin, sulpyrine, tiaramide hydrochloride, piroxicam, chlorpheniramine maleate, diphenylpyraline, diphenhydramine, clemastine fumarate, promethazine hydrochloride, diazepam, chlorpromazine hydrochloride, chlordiazepoxide, sulpiride, haloperidol, ethyl loflazepate, fluphenazine, thioridazine, fludiazepam, flunitrazepam, phenobarbital, amobarbital, cyclobarbital, triazolam, nitrazepam, nitroglycerin, isosorbide dinitrate, nitroglycol, erythritol tetranitrate, pentaerythritol tetranitrate, verapamyl, nifedipine, dipyridamole, diltiazem hydrochloride, propranolol, pindolol, clonidine, bupranolol, indenolol, nilvadipine, nipradilol, bucumolol, hydrazine hydrochloride, ace-inhibitor, calcium channel blocker, rescinnamine, hydrothiazide, benzylhydrochlorothiazide, cyclopenthiazide, furosemide, mefruside, trichlormethiazide, thiobromine, aciclovir, nalidixic acid, 5-FU, vincristine, adriamycin, bleomycin, mitomycin, cisplatin, therarubicin, metoclopramide, clebopride, scopolamine, domperidone, vitamin A, vitamin E, vitamin K, ergocalciferol, cholecalciferol, octotiamine, riboflavin tetrabutyrate, nitrazepam, clonazepam, baclofen, meprobamate, dextromethorphane, terbutaline, ephedrine, salbutamol, isoproterenol, trimetoquinol hydrochloride, prenylamine lactate, digitoxin, digoxin, lidocaine, benzocain, ethyl-p-aminobenzoate, ergot alkaloid, ifenprodil, pentamycin, amphotericin B, pyrrolnitrin, clotrimazole, benzalkonium chloride, nitrofurazone, nystatin, acetosulfamine, hydrocortisone, prednisolone, paramethasone, beclomethasone dipropionate, flumethasone, betamethasone, betamethasone valerate, dexamethasone, triamcinolone, triamcinolone acetonide, fluocinolone, fluocinolone acetonide, clobetasol propionate, progesterone, testosterone, estradiol, L-dopa, bromocriptine mesilate, epinephrine, ephedrine, pseudoephedrine, trihexyphenidyl hydrochloride, mazaticol hydrochloride, biperiden hydrochloride, TRH, LHRH, TNF, lymphotoxin, interferon, urokinase, insulin, calcitonin, their derivative polypeptides, prostaglandins, tolbutamide, colchicines, and nicotine.

13. A transdermal drug delivery device which comprises:

a) a backing layer;

b) the adhesive composition of claim 10 applied to at least a portion of the surface of the backing layer for securing the backing layer to skin; and

c) therapeutically effective amount of drug, the drug being contained in adhesive composition (b) and/or in an optional drug reservoir in, or attached to, backing layer (a).

14. The transdermal drug delivery device of claim 13 wherein the drug is at least one member selected from the group consisting of penicillins, cephalosporins, erythromycins, tetracyclines, macrolides, aminoglycosides, fosfomycins and rifampicins, mefenamic acid, flufenamic acid, indometacin, diclofenac, acetaminophen, alclofenac, oxyphenbutazone, phenylbutazone, ibuprofen, ketoprofen, salicylic acid, methyl salicylate, L-menthol, camphor, sulindac, naproxen, fenbufen, aspirin, sulpyrine, tiaramide hydrochloride, piroxicam, chlorpheniramine maleate, diphenylpyraline, diphenhydramine, clemastine fumarate, promethazine hydrochloride, diazepam, chlorpromazine hydrochloride, chlordiazepoxide, sulpiride, haloperidol, ethyl loflazepate, fluphenazine, thioridazine, fludiazepam, flunitrazepam, phenobarbital, amobarbital, cyclobarbital, triazolam and nitrazepam, nitroglycerin, isosorbide dinitrate, nitroglycol, erythritol tetranitrate, pentaerythritol tetranitrate, verapamyl, nifedipine, dipyridamole, diltiazem hydrochloride, propranolol, pindolol, clonidine, bupranolol, indenolol, nilvadipine, nipradilol, bucumolol, hydrazine hydrochloride, rescinnamine, hydrothiazide, benzylhydrochlorothiazide, cyclopenthiazide, furosemide, mefruside, trichlormethiazide, thiobromine, aciclovir, nalidixic acid, 5-FU, vincristine, adriamycin, bleomycin, mitomycin, cisplatin, therarubicin, metoclopramide, clebopride, scopolamine, domperidone, vitamin A, vitamin E, vitamin K, ergocalciferol, cholecalciferol, octotiamine, riboflavin tetrabutyrate, nitrazepam, clonazepam, baclofen, meprobamate, dextromethorphan, terbutaline, ephedrine, salbutamol, isoproterenol, trimetoquinol hydrochloride, prenylamine lactate, digitoxin, digoxin, lidocaine, benzocain, ethyl-p-aminobenzoate, ergot alkaloid, ifenprodil, pentamycin, amphotericin B, pyrrolnitrin, clotrimazole, benzalkonium chloride, nitrofurazone, nystatin, acetosulfamine, hydrocortisone, prednisolone, paramethasone, beclomethasone dipropionate, flumethasone, betamethasone, betamethasone valerate, dexamethasone, triamcinolone, triamcinolone acetonide, fluocinolone, fluocinolone acetonide, clobetasol propionate, progesterone, testosterone, estradiol, L-dopa, bromocriptine mesilate, trihexyphenidyl hydrochloride, mazaticol hydrochloride, biperiden hydrochloride, TRH, LHRH TNF, lymphotoxin, interferon, urokinase, insulin, calcitonin, their derivative polypeptides, prostaglandins, tolbutamide, colchicines, and nicotine.

15. The transdermal drug delivery device of claim 13 wherein the drug is present in the adhesive composition.

16. The transdermal drug delivery device of claim 13 possessing a drug reservoir, the drug being present in the drug reservoir.

17. In a transdermal drug delivery device which includes an adhesive component for affixing the device to skin, the improvement which comprises as adhesive component the adhesive composition of claim 10.

18. The composition of claim 1 wherein component (b) is high phenyl or low phenyl silicone.

19. The composition of claim 1 wherein component (b) is polyurethane adhesive.