IP Library Granted Patent US 9,587,149
Granted Patent B2
US 9,587,149 · App. 14/116,871 · Granted Mar 7, 2017

Pressure sensitive adhesive copolymer compositions

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Quick Facts
Patent No.
US 9,587,149
App. No.
14/116,871
Granted
Mar 7, 2017
Kind
B2
Abstract

This invention relates to a copolymer composition comprising vinyl ester of 2-ethyl hexanoic acid (VEHA), and particularly to pressure-sensitive adhesive compositions based on VEHA reacted with (meth)acrylate monomers. The present adhesive compositions provide a film with high cohesion and adhesion values, and more particularly to pressure-sensitive adhesive compositions based on VEHA reacted with (meth)acrylate monomers and VeoVa 10. The present adhesive compositions provide a film with high cohesion and adhesion values with Peel on Teflon of at least 2 N/inch.

Claims (41)

1. A pressure-sensitive adhesive copolymer composition comprising a reaction product consisting of:

60 to 85 weight % of vinyl ester of 2-ethyl hexanoic acid, and

one or more compounds selected from the group consisting of vinyl acetate, (meth)acrylate, (meth)acrylic acid, a vinyl ester of C3 to C18 carboxylic acid, and combinations thereof, wherein the total weight % of the copolymer is 100 weight % and wherein, when applied, comprises an adhesive layer having at least:

a. a 180° peel of from 7.5 N/25 mm to 10 N/25 mm, as measured by FTM-1 on stainless steel at room temperature after 24 hours;

b. a 180° peel of from 3.5 N/25 mm to 6 N/25 mm, as measured by FTM-1 on polyethylene at room temperature after 24 hours;

c. a 180° peel of from 7.5 N/25 mm to 12 N/25 mm, as measured by FTM-1 on glass at room temperature after 24 hours;

d. a shear holding of more than 5000 minutes, as measured by FTM-8 on stainless steel at room temperature after 24 hours; or

e. a loop-tack test of from 3 N to 10 N, as measured by FTM-9 on stainless steel at room temperature after 24 hours

or wherein, when applied, rises an adhesive layer having at least:

a. a 180° peel of from 7.5 N/25 mm to 15 N/25 mm, as measured by FTM-1 on stainless steel at room temperature after 24 hours;

b. a 180° peel of from 3.5 N/25 mm to 15 N/25 mm, as measured by FTM-1 on polyethylene at room temperature after 24 hours;

c. a 180° peel of from 7.5 N/25 mm to 15 N/25 mm, as measured by FTM-1 on glass at room temperature after 24 hours;

d. a shear holding of more than 500 minutes, as measured by FTM-8, on stainless steel at room temperature after 24 hours;

e. a loop-tack test of from 3 N to 10 N, as measured by FTM-9 on stainless steel at room temperature after 24 hours; or

f. a 180° peel of from 2N/25 mm to 7.5N/25 mm, as measured by FTM-1 on Teflon at room temperature after 24 hours.

2. The copolymer composition of claim 1 wherein the (meth)acrylate comprises the reaction products of ethylenically unsaturated carboxylic acids and C1 to C20 alcohols.

3. The copolymer composition of claim 2 wherein the (meth)acrylate is selected from the group of methyl(meth)acrylate, ethyl(meth)acrylate, propyl(meth)acrylate, n-butyl(meth)acrylate, isobutyl(meth)acrylate, t-butyl(meth)acrylate, pentyl(meth)acrylate, hexyl(meth)acrylate, cyclohexyl(meth)acrylate, benzyl(meth)acrylate, 2-ethylhexyl(meth)acrylate, heptyl(meth)acrylate, n-octyl(meth)acrylate, iso-octyl(meth)acrylate, nonyl(meth)acrylate, decyl(meth)acrylate, 2-propyl heptyl(meth)acrylate, undecyl(meth)acrylate, dodecyl(meth)acrylate, tridecyl(meth)acrylate, lauryl(meth)acrylate, stearyl(meth)acrylate, isobornyl(meth)acrylate, norbornyl(meth)acrylate, 4-tertbutylcyclohexyl(meth)acrylate, 3,3,5-trimethylcyclohexyl(meth)acrylate, dimethyl maleate, n-butyl maleate, alkylene glycol di(meth)acrylates, ethylene glycol di(meth)acrylate, 1,3-butylene glycol di(meth)acrylate, 1,4-butylene glycol di(meth)acrylate, propylene glycol(meth)acrylate, 1,6-hexanediol di(meth)acrylate, dipropylene glycol di(meth)acrylate, tripropylene glycol di(meth)acrylate, trimethylolpropane tri(meth)acrylate, cyclopentadienyl(meth)acrylate, carbodiimide(meth)acrylate, t-butylaminoethyl(meth)acrylate, 2-t-butylaminoethyl(meth)acrylate, and N,N-dimethylaminoethyl(meth)acrylate.

4. The copolymer composition of claim 1 made by an emulsion polymerization route.

5. The copolymer composition of claim 4 , wherein the reaction product has a residual level of each monomer of below 100 ppm.

6. A pressure-sensitive adhesive composition comprising:

the copolymer composition comprising a reaction product consisting of:

60 to 85 weight % of vinyl ester of 2-ethyl hexanoic acid, and

one or more compounds selected from the group consisting of vinyl acetate, (meth)acrylate, (meth)acrylic acid, a vinyl ester of C3 to C18 carboxylic acid, and combinations thereof, and

one or more of silane derivatives, a tackifier, an antifoam, a plasticizer, a surfactant, a wetting agent, a protective colloid, filler, a thickening agent, an antiseptic, a biocide, a dispersing agent, a pH adjusting agent, a corrosion inhibitor, an ultraviolet light stabilizer, a crosslinking promoter, an antioxidant, and another polymer, wherein, when applied, comprises an adhesive layer having at least:

a. a 180° peel of from 7.5 N/25 mm to 10 N/25 mm, as measured by FTM-1 on stainless steel at room temperature after 24 hours;

b. a 180° peel of from 3.5 N/25 mm to 6 N/25 mm, as measured by FTM-1 on polyethylene at room temperature after 24 hours;

c. a 180° peel of from 7.5 N/25 mm to 12 N/25 mm, as measured by FTM-1 on glass at room temperature after 24 hours;

d. a shear holding of more than 5000 minutes, as measured by FTM-8 on stainless steel at room temperature after 24 hours; or

e. a loop-tack test of from 3 N to 10 N, as measured by FTM-9 on stainless steel at room temperature after 24 hours,

or wherein, when applied, comprises an adhesive layer having at least:

a. a 180° peel of from 7.5 N/25 mm to 15 N/25 mm, as measured by FTM-1 on stainless steel at room temperature after 24 hours;

b. a 180° peel of from 3.5 N/25 mm to 15 N/25 mm, as measured by FTM-1 on polyethylene at room temperature after 24 hours;

c. a 180° peel of from 7.5 N/25 mm to 15 N/25 mm, as measured by FTM-1 on glass at room temperature after 24 hours;

d. a shear holding of more than 500 minutes, as measured by FTM-8, on stainless steel at room temperature after 24 hours;

e. a loop-tack test of from 3 N to 10 N, as measured by FTM-9 on stainless steel at room temperature after 24 hours; or

f. a 180° peel of from 2 N/25 mm to 7.5 N/25 mm, as measured by FTM-1 on Teflon at room temperature after 24 hours.

7. A pressure-sensitive adhesive composition of claim 6 , wherein the copolymer has a glass transition temperature (Tg) lower than −25° C.

8. A pressure-sensitive adhesive composition of claim 6 , wherein the copolymer has a glass transition temperature (Tg) in a range of from −5° C. to −80° C.

9. The copolymer composition of claim 1 wherein the copolymer has a glass transition temperature (Tg) lower than −5° C.

10. The copolymer composition of claim 1 wherein the copolymer has a glass transition temperature (Tg) in a range of from −5° C. to −80° C.

11. The pressure-sensitive adhesive composition of claim 6 , wherein the copolymer composition has a glass transition temperature (Tg) in a range of from −5° C. to −80° C.

Assignments (17)
RELEASE OF SECURITY INTEREST IN PATENTS (TERM LOAN) RECORDED AT REEL/FRAME 049741/0425 Recorded Mar 18, 2022
From: JPMORGAN CHASE BANK, N.A., AS COLLATERAL AGENT
To: HEXION INC.
Reel/Frame 059435/0473 →
RELEASE OF SECURITY INTEREST IN PATENTS (ABL) RECORDED AT REEL/FRAME 049740/0770 Recorded Mar 18, 2022
From: JPMORGAN CHASE BANK, N.A., AS COLLATERAL AGENT
To: HEXION INC.
Reel/Frame 059435/0490 →
SECURITY INTEREST Recorded Mar 18, 2022
From: HEXION INC.; HEXION INVESTMENTS INC.
To: GOLDMAN SACHS BANK USA, AS ADMINISTRATIVE AGENT
Reel/Frame 059436/0748 →
SECURITY INTEREST Recorded Mar 18, 2022
From: HEXION INC.; HEXION INVESTMENTS INC.
To: GOLDMAN SACHS BANK USA, AS ADMINISTRATIVE AGENT
Reel/Frame 059436/0823 →
SECURITY INTEREST Recorded Mar 18, 2022
From: HEXION INC.; HEXION INVESTMENTS INC.
To: ROYAL BANK OF CANADA, AS ADMINISTRATIVE AGENT
Reel/Frame 059436/0842 →
PATENT SECURITY INTEREST (ABL) Recorded Jul 12, 2019
From: HEXION INC.
To: JPMORGAN CHASE BANK, N.A., AS COLLATERAL AGENT
Reel/Frame 049740/0770 →
PATENT SECURITY INTEREST (TERM LOAN) Recorded Jul 12, 2019
From: HEXION INC.
To: JPMORGAN CHASE BANK, N.A., AS COLLATERAL AGENT
Reel/Frame 049741/0425 →
RELEASE OF SECURITY INTEREST IN PATENTS PREVIOUSLY RECORDED AT REEL/FRAME (030146/0970) Recorded Jul 9, 2019
From: JPMORGAN CHASE BANK, N.A., AS ADMINISTRATIVE AGENT AND COLLATERAL AGENT
To: HEXION INC. (FORMERLY KNOWN AS MOMENTIVE SPECIALTY CHEMICALS INC.)
Reel/Frame 049706/0264 →
PATENT SECURITY INTEREST ASSIGNMENT AGREEMENT Recorded Apr 3, 2019
From: WILMINGTON TRUST, NATIONAL ASSOCIATION, AS THE PRIOR COLLATERAL AGENT
To: WILMINGTON SAVINGS FUND SOCIETY, FSB, AS THE CURRENT COLLATERAL AGENT
Reel/Frame 048788/0617 →
RELEASE OF SECURITY INTEREST Recorded Feb 23, 2017
From: WILMINGTON TRUST, NATIONAL ASSOCIATION
To: HEXION INC. (FORMERLY KNOWN AS MOMENTIVE SPECIALTY CHEMICALS INC.)
Reel/Frame 041793/0602 →
SECURITY INTEREST Recorded Feb 13, 2017
From: HEXION INC.
To: WILMINGTON TRUST, NATIONAL ASSOCIATION, AS COLLATERAL AGENT
Reel/Frame 041693/0888 →
CHANGE OF NAME Recorded Jan 27, 2015
From: MOMENTIVE SPECIALTY CHEMICALS INC.
To: HEXION INC.
Reel/Frame 034817/0806 →
SECURITY AGREEMENT Recorded Feb 11, 2014
From: MOMENTIVE SPECIALTY CHEMICALS INC.
To: JPMORGAN CHASE BANK, N.A.
Reel/Frame 032239/0170 →
SECURITY AGREEMENT Recorded Jan 31, 2014
From: MOMENTIVE SPECIALTY CHEMICALS INC.
To: WILMINGTON TRUST, NATIONAL ASSOCIATION
Reel/Frame 032145/0764 →
SECURITY AGREEMENT Recorded Jan 31, 2014
From: MOMENTIVE SPECIALTY CHEMICALS INC.
To: WILMINGTON TRUST, NATIONAL ASSOCIATION
Reel/Frame 032145/0858 →
SECURITY AGREEMENT Recorded Jan 31, 2014
From: MOMENTIVE SPECIALTY CHEMICALS INC.
To: WILMINGTON TRUST COMPANY, AS COLLATERAL AGENT
Reel/Frame 032145/0966 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Nov 22, 2013
From: HAVAUX, NATHALIE; SIMAL, FRANCOIS; KAMENEVA, OLGA
To: MOMENTIVE SPECIALTY CHEMICALS INC.
Reel/Frame 031656/0827 →