Patent US3933936A successfully refreshed from Google Patents.
US3933936A
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Rapid setting adhesive compounds
Assignee: Dow Chemical Co
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Filing: 1973-02-20
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Granted: 1976-01-20
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Expires: 1993-02-20
Abstract
Abstract Mixtures of a curable phenolic resin and an organic diaziridine are strong adhesives curable in a relatively short time at moderate temperatures to make strong bonds with wood, metal, and plastics.
Inventors
- 👤 Harry A. Smith
- 👤 Erwin H. Kobel
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-11-05 11:21
CPC Classifications
C; C09; C09J; C09J161/00; C09J161/04; C09J161/06; C08; C08K; C08K5/00; C08K5/16; C08K5/34; C08L; C08L61/00; C08L61/04; C08L61/06; C08L75/00; C08L75/04; C08L75/08; Y; Y10; Y10T; Y10T428/00; Y10T428/31504; Y10T428/31551; Y10T428/31594; Y10T428/31678; Y10T428/31681
Claims Analysis
Total Claims: 12
Claim 1
Independent Claim
183 words
An adhesive composition comprising a curable phenolic-formaldehyde resin and from about 0.5 to about 20 parts by weight of an organic diaziridine, wherein said phenolic-formaldehyde resin is a novolac or a resole obtained by reacting formaldehyde with a monohydric or dihydric phenol or mixture thereof having at least two aromatic ring positions ortho or para to a phenolic hydroxyl group unsubstituted and capable of reaction with formaldehyde in the presence of a basic, neutral, or acidic condensation catalyst wherein said diaziridine has the formula ##EQU4## and R is a radical represented by the formula ##EQU5## wherein m is zero or one, n is two or three, and R' is an alkylene radical of 2--10 carbon atoms, an arylene hydrocarbon radical or 6-14 carbon atoms, or the residue of the compound obtained by the reaction of two moles of an aromatic or aliphatic diisocyanate with a diol, the diol being ethylene glycol, propylene glycol, a corresponding polyglycol or molecular weight up to about 1000, Bisphenol A, or the adduct of Bisphenol A with two to about 20 moles of ethylene oxide or propylene oxide.
Claim 2
Dependent Claim
183 words
An adhesive composition comprising a curable phenolic-formaldehyde resin and from about 0.5 to about 20 parts by weight of an organic diaziridine, wherein said phenolic-formaldehyde resin is a novolac or a resole obtained by reacting formaldehyde with a monohydric or dihydric phenol or mixture thereof having at least two aromatic ring positions ortho or para to a phenolic hydroxyl group unsubstituted and capable of reaction with formaldehyde in the presence of a basic, neutral, or acidic condensation catalyst wherein said diaziridine has the formula ##EQU4## and R is a radical represented by the formula ##EQU5## wherein m is zero or one, n is two or three, and R' is an alkylene radical of 2--10 carbon atoms, an arylene hydrocarbon radical or 6-14 carbon atoms, or the residue of the compound obtained by the reaction of two moles of an aromatic or aliphatic diisocyanate with a diol, the diol being ethylene glycol, propylene glycol, a corresponding polyglycol or molecular weight up to about 1000, Bisphenol A, or the adduct of Bisphenol A with two to about 20 moles of ethylene oxide or propylene oxide.
Claim 3
Dependent Claim
64 words
The composition of claim 1 wherein the diaziridine is defined by the formula when R' is the residue of the compound obtained by the reaction of two moles of aromatic hydrocarbon diisocyanate with a mole of an alkylene glycol or polyalkylene glycol of molecular weight up to about 1000 wherein the term alkylene is defined as ethylene or propylene and wherein m is zero.
Claim 4
Dependent Claim
28 words
The composition of claim 2 wherein the phenolic resin is obtained by reacting phenol with about 0.5-2.5 moles of formaldehyde in the presence of an essentially neutral catalyst.
Claim 5
Dependent Claim
59 words
The composition of claim 3 wherein the phenolic resin is first modified by reacting it at about 50°C. to about the boiling point of the reaction mixture with about 0.05-0.5 g. mole per 100 g. of resin of at least one aromatic amine of the group consisting of aniline, ar-(lower alkyl)aniline, ar-(lower alkoxy)aniline, m-hydroxyaniline, phenylenediamine, oxydianiline, and methylene dianiline.
Claim 6
Dependent Claim
54 words
The composition of claim 4 wherein the phenolic resin has been modified by reaction with aniline and m-hydroxyaniline and R' in the diaziridine formula is the residue of the product of reaction of two moles of tolylene diisocyanate with a mole of propylene glycol or polypropylene glycol of molecular weight up to about 1000.
Claim 7
Dependent Claim
20 words
The composition of claim 5 wherein the glycol reactant is polypropylene glycol with an average molecular weight of about 360.
Claim 8
Dependent Claim
13 words
The composition of claim 2 wherein the phenolic resin is a resorcinol-formaldehyde resin.
Claim 9
Dependent Claim
68 words
The composition of claim 1 wherein the diaziridine is defined by the formula when R' is the residue of the compound obtained by the reaction of two moles of aromatic hydrocarbon diisocyanate with a mole of an alkylene glycol or polyalkylene glycol or molecular weight up to about 1000 wherein the term alkylene is defined as ethylene or propylene and wherein m is one and n is two.
Claim 10
Dependent Claim
28 words
The composition of claim 8 wherein the phenolic resin is obtained by reacting phenol with about 0.5-2.5 moles of formaldehyde in the presence of an essentially neutral catalyst.
Claim 11
Dependent Claim
59 words
The composition of claim 9 wherein the phenolic resin is first modified by reacting it at about 50°C. to about the boiling point of the reaction mixture with about 0.05-0.5 g. mole per 100 g. of resin of at least one aromatic amine of the group consisting of aniline, ar-(lower alkyl)aniline, ar-(lower alkoxy)aniline, m-hydroxyaniline, phenylenediamine, oxydianiline and methylene dianiline.
Claim 12
Dependent Claim
13 words
The composition of claim 8 wherein the phenolic resin is a resorcinol-formaldehyde resin.
References Cited (Backward Citations)
USPTO Annuity & Maintenance Windows
| Annuity Stage | Window Opens | Payment Deadline | Surcharge Period Until | Estimated Fee | Status |
|---|---|---|---|---|---|
| 3.5 Years (Year 4) | 1979-01-19 | 1979-07-21 | 1980-01-20 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1983-01-19 | 1983-07-21 | 1984-01-20 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1987-01-19 | 1987-07-21 | 1988-01-20 | $7700.00 | Window Closed / Lapsed |