Patent US4732841A successfully refreshed from Google Patents.
US5616629A
Expired / Lapsed
US
⏱️ 0.0 years remaining
Radiation-curable organopolysiloxane release compositions
Assignee: Avery Dennison Corp
•
Filing: 1995-02-27
•
Granted: 1997-04-01
•
Expires: 2015-02-27
Abstract
Abstract A radiation-curable release composition is disclosed which comprises: (A) an organopolysiloxane represented by the formula RSi(CH.sub.3).sub.2 --O--(Si(CH.sub.3).sub.2 O).sub.n (Si(CH 3 )(R)O) m Si(CH 3 ) 2 R (I) wherein in Formula (I), each R is --R 1 --O(O)C--C(R 2 )═CH 2 , --R 1 --O--C(R 2 )═CH 2 or is derived from an organic molecule containing both ethylenic unsaturation and epoxide functionality; R 1 is a hydrocarbylene group; each R 2 is independently hydrogen or a methyl or ethyl group; m is a number from about 1 to about 15; and n is a number from about 50 to about 300; and (B) an organosiloxane copolymer represented by the formula (R.sub.3 SiO).sub.x (SiO.sub.4/2).sub.y (II) wherein in Formula (II), each R is independently a hydrocarbon group or a group represented by the formula --O(O)C--C(R*)═CH.sub.2 wherein R* is hydrogen or a methyl or ethyl group; x is a number from about 0.25 to about 75; y is a number from about 1 to about 56; and the ratio of x to y is from about 0.3:1 to about 1.5. In one embodiment, the inventive release composition further comprises (C) an acrylate represented by the formula CH.sub.2 ═C(R**)--C(O)O--R.sup.2 (III) wherein in Formula (III), R** is hydrogen or a methyl or ethyl group, and R 2 is a hydrocarbon group of about 10 to about 24 carbon atoms. A method of producing release-coated substrates, the release-crated articles thus produced, and multi-layer articles or constructions incorporating a release layer also are disclosed. When the release compositions are cured such as by radiation, the cured compositions exhibit a desirable high and controlled release force at high speeds such as the speeds utilized in label processing.
Inventors
- 👤 Thanh V. Nguyen
- 👤 John Allen
- 👤 Qun Yu
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-11-04 22:30
CPC Classifications
C; C08; C08F; C08F290/00; C08F290/02; C08F290/06; C08F290/068; B; B32; B32B; B32B9/00; B32B9/04; C08L; C08L83/00; C08L83/04; C08L83/06; C09; C09D; C09D183/00; C09D183/04; C09D183/06; C09J; C09J7/00; C09J7/20; C09J7/21; C09J7/30; C09J7/38; C09J7/40; C09J7/401; C09J2301/00; C09J2301/40; C09J2301/414; C09J2301/416; C09J2400/00; C09J2400/20; C09J2400/22; C09J2400/226; C09J2400/26; C09J2400/263; C09J2400/28; C09J2400/283; C09J2433/00; C09J2433/005; C09J2483/00; C09J2483/005
Claims Analysis
Total Claims: 27
Claim 1
Independent Claim
179 words
A radiation-curable release composition, comprising: (A) an organopolysiloxane represented by the formula RSi(CH.sub.3).sub.2 --O--(Si(CH.sub.3).sub.2 O).sub.n (Si(CH.sub.3)(R)O).sub.m Si(CH.sub.3).sub.2 R (I) wherein in Formula (I), each R is --R 1 --O(O)C--C(R 2 )═CH or --R 1 --O--C(R 2 )═CH 2 ; R 1 is a hydrocarbylene group; each R 2 is independently hydrogen or a methyl or ethyl group; m is a number from about 1 to about 15; and n is a number from about 50 to about 300; and (B) an organosiloxane copolymer represented by the formula (R.sub.3 SiO).sub.x (SiO.sub.4/2).sub.y (II) wherein in Formula (II), each R is independently a hydrocarbon group or a group represented by the formula O(O)C--C(R*)═CH.sub.2 wherein R* is hydrogen or a methyl or ethyl group; x is a number from about 0.25 to about 75; y is a number from about 1 to about 56; the ratio of x to y is from about 0.3:1 to about 1.5, with the proviso when R in Formula (I) is --R 1 --O(O)C--C(R 2 )═CH 2 , R in Formula (II) is other than --O(O)C--C(R*)═CH 2 .
Claim 2
Dependent Claim
179 words
A radiation-curable release composition, comprising: (A) an organopolysiloxane represented by the formula RSi(CH.sub.3).sub.2 --O--(Si(CH.sub.3).sub.2 O).sub.n (Si(CH.sub.3)(R)O).sub.m Si(CH.sub.3).sub.2 R (I) wherein in Formula (I), each R is --R 1 --O(O)C--C(R 2 )═CH or --R 1 --O--C(R 2 )═CH 2 ; R 1 is a hydrocarbylene group; each R 2 is independently hydrogen or a methyl or ethyl group; m is a number from about 1 to about 15; and n is a number from about 50 to about 300; and (B) an organosiloxane copolymer represented by the formula (R.sub.3 SiO).sub.x (SiO.sub.4/2).sub.y (II) wherein in Formula (II), each R is independently a hydrocarbon group or a group represented by the formula O(O)C--C(R*)═CH.sub.2 wherein R* is hydrogen or a methyl or ethyl group; x is a number from about 0.25 to about 75; y is a number from about 1 to about 56; the ratio of x to y is from about 0.3:1 to about 1.5, with the proviso when R in Formula (I) is --R 1 --O(O)C--C(R 2 )═CH 2 , R in Formula (II) is other than --O(O)C--C(R*)═CH 2 .
Claim 3
Dependent Claim
46 words
The composition of claim 1 further comprising (C) an acrylate represented by the formula CH.sub.2 ═C(R**)--C(O)O--R.sup.2 (III) wherein in Formula (III), R 1 is hydrogen or a methyl or ethyl group, and R 2 is a hydrocarbon group of about 10 to about 25 carbon atoms.
Claim 4
Dependent Claim
27 words
The composition of claim 2 wherein in Formula (III), R** is hydrogen and R 2 is a hydrocarbon group of about 10 to about 18 carbon atoms.
Claim 5
Dependent Claim
10 words
The composition of claim 1 further comprising (D) a photoinitiator.
Claim 6
Dependent Claim
47 words
The composition of claim 4 wherein said photoinitiator (D) is a compound selected from the group consisting of: 2,2-diethoxyacetophenone; 2- or 3- or 4-bromoacetophenone; benzoin; benzophenone; 4-chlorobenzophenone; 4-phenylbenzophenone; benzoquinone; 1-chloroanthroquinone; p-diacetyl-benzene; 9,10-dibromoanthracene; 1,3-diphenyl-2-propanone; 1,4-naphthyl-phenyl ketone; 2,3-pentenedione; propiophenone; chlorothioxanthone; xanthone; fluorenone; and mixtures of two or more thereof.
Claim 7
Dependent Claim
20 words
The composition of claim 1 further comprising (E) at least one acrylated or methacrylated organic polyhydroxy compound or polyamino compound.
Claim 8
Dependent Claim
55 words
The composition of claim 6 wherein component (E) is a compound represented by the formula R--(--CO--C(X)═CH.sub.2).sub.n (IV) wherein in Formula (IV), R is derived from a polyhydroxy compound or a polyamine or an organic compound containing hydroxy groups and amino groups, X is hydrogen or methyl, and n is an integer of at least 2.
Claim 9
Dependent Claim
49 words
The composition of claim 6 wherein component (E) is a compound selected from the group consisting of glycerol diacrylate, diethylene glycol diacrylate, 1,6-hexanediol diacrylate, triethylene glycol diacrylate, trimethylolpropane triacrylate, neopentylglycol di-, tri-, or tetraacrylate, tripropylene glycol diacrylate, 1,6-hexanediol dimethacrylate, ethylene glycol dimethacrylate, and mixtures of two or more thereof.
Claim 10
Dependent Claim
13 words
The composition of claim 6 wherein component (E) is an acrylated amine oligomer.
Claim 11
Dependent Claim
25 words
The composition of claim 1 wherein in Formula (I), R 1 is an aliphatic, cycloaliphatic or aromatic group of up to about 10 carbon atoms.
Claim 12
Dependent Claim
14 words
The composition of claim 1 wherein in Formula (I), each R 2 is hydrogen.
Claim 13
Dependent Claim
41 words
The composition of claim 1 wherein in Formula (I), R is --(CH 2 ) 6 OC(O)CH═CH 2 , m is in the range of about 1 to about 15, and n is in the range of about 50 to about 300.
Claim 14
Dependent Claim
26 words
The composition of claim 1 wherein in Formula (I), R is --(CH 2 ) 6 OC(O)CH═CH 2 , m is 6, and n is about 136.
Claim 15
Dependent Claim
26 words
The composition of claim 1 wherein in Formula (I), R is --(CH 2 ) 6 OC(O)CH═CH 2 , m is 2, and n is about 100.
Claim 16
Dependent Claim
13 words
The composition of claim 1 wherein in Formula (I), R is vinyl ether.
Claim 17
Dependent Claim
14 words
The composition of claim 1 wherein in Formula (II), R is an acrylic group.
Claim 18
Dependent Claim
14 words
The composition of claim 1 wherein in Formula (II), R is a hydrocarbon group.
Claim 19
Dependent Claim
182 words
A radiation-curable release composition, comprising: (A) an organopolysiloxane represented by the formula RSi(CH.sub.3).sub.2 --O--(Si(CH.sub.3).sub.2 O).sub.n (Si(CH.sub.3)(R)O).sub.m Si(CH.sub.3).sub.2 R (I) wherein n Formula (I), each R is --R 1 --O(O)C--C(R 2 )═CH 2 , R 1 is a hydrocarbylene group, R 2 is hydrogen or a methyl or ethyl group, m is a number from about 1 to about 15, and n is a number from about 50 to about 300; (B) an organosiloxane copolymer represented by the formula (R.sub.3 SiO).sub.x (SiO.sub.4/2).sub.y (II) wherein in Formula (II), each R is independently a hydrocarbon group or a group represented by the formula --O(O)C--C(R*)═CH.sub.2 wherein R* is hydrogen or a methyl or ethyl group; x is a number from about 0.25 to about 75; y is a number from about 1 to abut 56; the ratio of x to y is from about 0.3:1 to about 1.3:1; and (C) an acrylate represented by the formula CH.sub.2 ═C(R**)--C(O)OR.sup.2 wherein in Formula (III), R** is hydrogen or a methyl or ethyl group, and R 2 is a hydrocarbon group of about 10 to about 24 carbon atoms.
Claim 20
Dependent Claim
182 words
A radiation-curable release composition, comprising: (A) an organopolysiloxane represented by the formula RSi(CH.sub.3).sub.2 --O--(Si(CH.sub.3).sub.2 O).sub.n (Si(CH.sub.3)(R)O).sub.m Si(CH.sub.3).sub.2 R (I) wherein n Formula (I), each R is --R 1 --O(O)C--C(R 2 )═CH 2 , R 1 is a hydrocarbylene group, R 2 is hydrogen or a methyl or ethyl group, m is a number from about 1 to about 15, and n is a number from about 50 to about 300; (B) an organosiloxane copolymer represented by the formula (R.sub.3 SiO).sub.x (SiO.sub.4/2).sub.y (II) wherein in Formula (II), each R is independently a hydrocarbon group or a group represented by the formula --O(O)C--C(R*)═CH.sub.2 wherein R* is hydrogen or a methyl or ethyl group; x is a number from about 0.25 to about 75; y is a number from about 1 to abut 56; the ratio of x to y is from about 0.3:1 to about 1.3:1; and (C) an acrylate represented by the formula CH.sub.2 ═C(R**)--C(O)OR.sup.2 wherein in Formula (III), R** is hydrogen or a methyl or ethyl group, and R 2 is a hydrocarbon group of about 10 to about 24 carbon atoms.
Claim 21
Dependent Claim
168 words
A radiation-curable release composition, comprising: (A) an organopolysiloxane represented by the formula RSi(CH.sub.3).sub.2 --O--(Si(CH.sub.3).sub.2 O).sub.n (Si(CH.sub.3)(R)O).sub.m Si(CH.sub.3).sub.2 R (I) wherein in Formula (I), R is --(CH 2 ) 6 OC(O)CH═CH 2 , m is a number in the range of about 2 to about 10 and n is a number in the range of about 120 to about 150; (B) an organosiloxane copolymer represented by the formula (R.sub.3 SiO).sub.x (SiO.sub.4/2).sub.y (II) wherein in Formula (II), each R is independently a vinyl group; x is a number from about 1 to about 75; y is a number from about 1 to about 56; and the ratio of x to y is from about 0.3:1 to about 1.3:1; (C) dodecyl acrylate; (E-1) an acrylated amine oligomer; and (E-2) at least one compound selected from the group consisting of glycerol diacrylate, diethylene glycol diacrylate, 1,6-hexanediol diacrylate, triethylene glycol diacrylate, trimethylolpropane triacrylate, neopentylglycol di-, tri-, or tetraacrylate, tripropylene glycol diacrylate, 1,6-hexanediol dimethacrylate, ethylene glycol dimethacrylate, and mixtures of two or more thereof.
Claim 22
Dependent Claim
168 words
A radiation-curable release composition, comprising: (A) an organopolysiloxane represented by the formula RSi(CH.sub.3).sub.2 --O--(Si(CH.sub.3).sub.2 O).sub.n (Si(CH.sub.3)(R)O).sub.m Si(CH.sub.3).sub.2 R (I) wherein in Formula (I), R is --(CH 2 ) 6 OC(O)CH═CH 2 , m is a number in the range of about 2 to about 10 and n is a number in the range of about 120 to about 150; (B) an organosiloxane copolymer represented by the formula (R.sub.3 SiO).sub.x (SiO.sub.4/2).sub.y (II) wherein in Formula (II), each R is independently a vinyl group; x is a number from about 1 to about 75; y is a number from about 1 to about 56; and the ratio of x to y is from about 0.3:1 to about 1.3:1; (C) dodecyl acrylate; (E-1) an acrylated amine oligomer; and (E-2) at least one compound selected from the group consisting of glycerol diacrylate, diethylene glycol diacrylate, 1,6-hexanediol diacrylate, triethylene glycol diacrylate, trimethylolpropane triacrylate, neopentylglycol di-, tri-, or tetraacrylate, tripropylene glycol diacrylate, 1,6-hexanediol dimethacrylate, ethylene glycol dimethacrylate, and mixtures of two or more thereof.
Claim 23
Dependent Claim
176 words
A radiation-curable release composition, comprising: (A) an organopolysiloxane represented by the formula RSi(CH.sub.3).sub.2 --O--(Si(CH.sub.3).sub.2 O).sub.n (Si(CH.sub.3)(R)O).sub.m Si(CH.sub.3).sub.2 R (I) wherein in Formula (I), each R is --R 1 --O--C(R 2 )═CH 2 or is derived by addition reaction from an organic molecule containing both ethylenic unsaturation and epoxide functionality; R 1 is a hydrocarbylene group; each R 2 is independently hydrogen or a methyl or ethyl group; m is a number from about 1 to about 15; and n is a number from about 50 to about 300; and (B) an organosiloxane copolymer represented by the formula (R.sub.3 SiO).sub.x (SiO.sub.4/2).sub.y (II) wherein in Formula (II), each R is independently a hydrocarbon group or a group represented by the formula --O(O)C--C(R*)═CH.sub.2 wherein R* is hydrogen or a methyl or ethyl group, with the proviso that at least one R must be --O(O)C--C(R*)═CH 2 ; x is a number from about 0.25 to about 75; y is a number from about 1 to about 56; the ratio of x to y is from about 0.3:1 to about 1.5.
Claim 24
Dependent Claim
176 words
A radiation-curable release composition, comprising: (A) an organopolysiloxane represented by the formula RSi(CH.sub.3).sub.2 --O--(Si(CH.sub.3).sub.2 O).sub.n (Si(CH.sub.3)(R)O).sub.m Si(CH.sub.3).sub.2 R (I) wherein in Formula (I), each R is --R 1 --O--C(R 2 )═CH 2 or is derived by addition reaction from an organic molecule containing both ethylenic unsaturation and epoxide functionality; R 1 is a hydrocarbylene group; each R 2 is independently hydrogen or a methyl or ethyl group; m is a number from about 1 to about 15; and n is a number from about 50 to about 300; and (B) an organosiloxane copolymer represented by the formula (R.sub.3 SiO).sub.x (SiO.sub.4/2).sub.y (II) wherein in Formula (II), each R is independently a hydrocarbon group or a group represented by the formula --O(O)C--C(R*)═CH.sub.2 wherein R* is hydrogen or a methyl or ethyl group, with the proviso that at least one R must be --O(O)C--C(R*)═CH 2 ; x is a number from about 0.25 to about 75; y is a number from about 1 to about 56; the ratio of x to y is from about 0.3:1 to about 1.5.
Claim 25
Dependent Claim
16 words
The composition of claim 20 wherein in Formula (I), R is derived from 4-vinyl cyclohexene oxide.
Claim 26
Dependent Claim
147 words
A radiation-curable release composition, comprising: (A) an organopolysiloxane represented by the formula RSi(CH.sub.3).sub.2 --O--(Si(CH.sub.3).sub.2 O).sub.n (Si(CH.sub.3)(R)O).sub.m Si(CH.sub.3).sub.2 R (I) wherein in Formula (I), each R is --R 1 --O--C(R 2 )═CH 2 ; R 1 is a hydrocarbylene group; each R 2 is independently hydrogen or a methyl or ethyl group; m is a number from about 1 to about 15; and n is a number from about 50 to about 300; and (B) an organosiloxane copolymer represented by the formula (R.sub.3 SiO).sub.x (SiO.sub.4/2).sub.y (II) wherein in Formula (II), each R is independently a hydrocarbon group or a group represented by the formula --O(O)C--C(R*)═CH.sub.2 wherein R* is hydrogen or a methyl or ethyl group; x is a number from about 0.25 to about 75; y is a number from about 1 to about 56; the ratio of x to y is from about 0.3:1 to about 1.5.
Claim 27
Dependent Claim
147 words
A radiation-curable release composition, comprising: (A) an organopolysiloxane represented by the formula RSi(CH.sub.3).sub.2 --O--(Si(CH.sub.3).sub.2 O).sub.n (Si(CH.sub.3)(R)O).sub.m Si(CH.sub.3).sub.2 R (I) wherein in Formula (I), each R is --R 1 --O--C(R 2 )═CH 2 ; R 1 is a hydrocarbylene group; each R 2 is independently hydrogen or a methyl or ethyl group; m is a number from about 1 to about 15; and n is a number from about 50 to about 300; and (B) an organosiloxane copolymer represented by the formula (R.sub.3 SiO).sub.x (SiO.sub.4/2).sub.y (II) wherein in Formula (II), each R is independently a hydrocarbon group or a group represented by the formula --O(O)C--C(R*)═CH.sub.2 wherein R* is hydrogen or a methyl or ethyl group; x is a number from about 0.25 to about 75; y is a number from about 1 to about 56; the ratio of x to y is from about 0.3:1 to about 1.5.
References Cited (Backward Citations)
US2676182A
Cited
US2857356A
Cited
US4125470A
Cited
US4087478A
Cited
US4201808A
Cited
US4421904A
Cited
US4518727A
Cited
US4576999A
Cited
US4547431A
Cited
US4678846A
Cited
US4554296A
Cited
US4568566A
Cited
US4624998A
Cited
US4952657A
Cited
US5198476A
Cited
US5310601A
Cited
US5217805A
Cited
US5240971A
Cited
US5332797A
Cited
US5279860A
Cited
US5360833A
Cited
USPTO Annuity & Maintenance Windows
| Annuity Stage | Window Opens | Payment Deadline | Surcharge Period Until | Estimated Fee | Status |
|---|---|---|---|---|---|
| 3.5 Years (Year 4) | 2000-03-31 | 2000-09-30 | 2001-04-01 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 2004-03-31 | 2004-09-30 | 2005-04-01 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 2008-03-31 | 2008-09-30 | 2009-04-01 | $7700.00 | Window Closed / Lapsed |