Temperature switchable adhesives comprising crystallizable abietic acid derivative-based tackifiers
First Claim
Patent Images
1. A composition comprising:
- a) at least one elastomer; and
b) at least one crystallizable abietic acid derivative-based tackifier having the formula;
wherein;
(i) R is a linear or branched, substituted or unsubstituted alkyl or trans alkenyl group having from 12 to 30 carbon atoms, a fluoroalkyl or trans fluoroalkenyl group having from 12 to 30 carbon atoms, phenyl, benzyl, phenolic, naphthalenic, or hydroquinoid;
(ii) R1, R2, R1′
, and R2′
are independently H, a linear substituted or unsubstituted alkyl group having 1 or 2 carbon atoms, a linear or branched, substituted or unsubstituted alkyl group having 3 carbon atoms, a linear substituted or unsubstituted alkenyl group having 2 carbon atoms, or a linear or branched, substituted or unsubstituted alkenyl group having 3 carbon atoms, provided that if the ring containing R1 and R2 is aromatic, then R1 and R2 are not present, and if the ring containing R1′ and
R2′
is aromatic, then R1′ and
R2′
are not present;
(iii) R3 and R3′
are independently H, a linear substituted or unsubstituted alkyl group having 1 or 2 carbon atoms, a linear or branched, substituted or unsubstituted alkyl group having 3 carbon atoms, a linear substituted or unsubstituted alkenyl group having 2 carbon atoms, or a linear or branched, substituted or unsubstituted alkenyl group having 3 carbon atoms;
(iv) R′ and
R″
are independently R, H, methyl, ethyl, glycerol, or glycol;
(v) M is O or NRL;
(vi) the six-membered rings have carbon-carbon single bonds or a combination of carbon-carbon single bonds and carbon-carbon double bonds;
(vii) the six membered rings of (I) and (III) are independently aromatic or non-aromatic, provided that no more than two of the rings are aromatic;
(viii) the six membered rings of (II) are independently aromatic or non-aromatic, provided that no more than four of the rings are aromatic;
(ix) L is an optional spacer selected from the group consisting of;
—
(CO)—
, —
O—
(CO)—
, —
OCH2—
, vinyl, amide, —
(CO)O(CHR4—
CHR5O)nCH2—
, and —
(CO)O(CH2)mOCH2, wherein n is 1 to 4, m is 1 to 4, R4 and R5 are independently H, methyl, or ethyl; and
(x) the ratio of said elastomer to crystallizable abietic acid derivative-based tackifier is from about 3;
1 to about 1;
5 by weight.
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Accused Products
Abstract
Temperature switchable pressure sensitive adhesives comprising an elastomer and a crystallizable abietic acid derivative as tackifier are described. These pressure sensitive adhesives exhibit a sharp reduction in peel strength when the temperature is raised above the switching temperature. The adhesive properties of these adhesives may be readily tuned by adjusting the ratio of the elastomer and the crystallizable tackifier, and by altering the crystallizabe group on the tackifier. The temperature switchable pressure sensitive adhesives have use in medical, consumer, and industrial applications.
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Citations
17 Claims
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1. A composition comprising:
-
a) at least one elastomer; and
b) at least one crystallizable abietic acid derivative-based tackifier having the formula;
wherein;
(i) R is a linear or branched, substituted or unsubstituted alkyl or trans alkenyl group having from 12 to 30 carbon atoms, a fluoroalkyl or trans fluoroalkenyl group having from 12 to 30 carbon atoms, phenyl, benzyl, phenolic, naphthalenic, or hydroquinoid;
(ii) R1, R2, R1′
, and R2′
are independently H, a linear substituted or unsubstituted alkyl group having 1 or 2 carbon atoms, a linear or branched, substituted or unsubstituted alkyl group having 3 carbon atoms, a linear substituted or unsubstituted alkenyl group having 2 carbon atoms, or a linear or branched, substituted or unsubstituted alkenyl group having 3 carbon atoms, provided that if the ring containing R1 and R2 is aromatic, then R1 and R2 are not present, and if the ring containing R1′ and
R2′
is aromatic, then R1′ and
R2′
are not present;
(iii) R3 and R3′
are independently H, a linear substituted or unsubstituted alkyl group having 1 or 2 carbon atoms, a linear or branched, substituted or unsubstituted alkyl group having 3 carbon atoms, a linear substituted or unsubstituted alkenyl group having 2 carbon atoms, or a linear or branched, substituted or unsubstituted alkenyl group having 3 carbon atoms;
(iv) R′ and
R″
are independently R, H, methyl, ethyl, glycerol, or glycol;
(v) M is O or NRL;
(vi) the six-membered rings have carbon-carbon single bonds or a combination of carbon-carbon single bonds and carbon-carbon double bonds;
(vii) the six membered rings of (I) and (III) are independently aromatic or non-aromatic, provided that no more than two of the rings are aromatic;
(viii) the six membered rings of (II) are independently aromatic or non-aromatic, provided that no more than four of the rings are aromatic;
(ix) L is an optional spacer selected from the group consisting of;
—
(CO)—
, —
O—
(CO)—
, —
OCH2—
, vinyl, amide,—
(CO)O(CHR4—
CHR5O)nCH2—
, and —
(CO)O(CH2)mOCH2,wherein n is 1 to 4, m is 1 to 4, R4 and R5 are independently H, methyl, or ethyl; and
(x) the ratio of said elastomer to crystallizable abietic acid derivative-based tackifier is from about 3;
1 to about 1;
5 by weight. - View Dependent Claims (2, 3, 4, 5, 6, 7, 8, 9, 10, 11)
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12. A method for imparting temperature switchable properties to an elastomer comprising the steps of:
-
a) providing at least one elastomer; and
b) mixing the at least one elastomer with at least one crystallizable abietic acid derivative-based tackifier having the formula;
wherein;
(i) R is a linear or branched, substituted or unsubstituted alkyl or trans alkenyl group having from 12 to 30 carbon atoms, a fluoroalkyl or trans fluoroalkenyl group having from 12 to 30 carbon atoms, phenyl, benzyl, phenolic, naphthalenic, or hydroquinoid;
(ii) R1, R2, R1′
, and R2′
are independently H, a linear substituted or unsubstituted alkyl group having 1 or 2 carbon atoms, a linear or branched, substituted or unsubstituted alkyl group having 3 carbon atoms, a linear substituted or unsubstituted alkenyl group having 2 carbon atoms, or a linear or branched, substituted or unsubstituted alkenyl group having 3 carbon atoms, provided that if the ring containing R1 and R2 is aromatic, then R1 and R2 are not present, and if the ring containing R1′ and
R2′
is aromatic, then R1′ and
R2′
are not present;
(iii) R3 and R3′
are independently H, a linear substituted or unsubstituted alkyl group having 1 or 2 carbon atoms, a linear or branched, substituted or unsubstituted alkyl group having 3 carbon atoms, a linear substituted or unsubstituted alkenyl group having 2 carbon atoms, or a linear or branched, substituted or unsubstituted alkenyl group having 3 carbon atoms;
(iv) R′ and
R″
are independently R, H, methyl, ethyl, glycerol, or glycol;
(v) M is O or NRL;
(vi) the six-membered rings have carbon-carbon single bonds or a combination of carbon-carbon single bonds and carbon-carbon double bonds;
(vii) the six membered rings of (I) and (III) are independently aromatic or non-aromatic, provided that no more than two of the rings are aromatic;
(viii) the six membered rings of (II) are independently aromatic or non-aromatic, provided that no more than four of the rings are aromatic;
(ix) L is an optional spacer selected from the group consisting of;
—
(CO)—
, —
O—
(CO)—
, —
OCH2—
, vinyl, amide,—
(CO)O(CHR4—
CHR5O)nCH2—
, and —
(CO)O(CH2)mOCH2,wherein n is 1 to 4, m is 1 to 4, R4 and R5 are independently H, methyl, or ethyl; and
(x) the ratio of said elastomer to crystallizable abietic acid derivative-based tackifier is from about 3;
1 to about 1;
5 by weight. - View Dependent Claims (13, 14, 15, 16, 17)
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Specification