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US3878136A Expired / Lapsed US ⏱️ 0.0 years remaining

Process for the manufacture of dispersions of thermosetting phenolic reaction products

Assignee: Hoechst AG
•
Filing: 1973-06-18
•
Granted: 1975-04-15
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Expires: 1993-06-18
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Abstract

Abstract Subject of the invention is a process for the manufacture of water-dilutable, self-emulsified, aqueous dispersions of thermosetting reaction products of monohydroxybenzene compounds, or mixtures of monohydroxybenzene compounds, with formaldehyde and secondary amines in water, wherein these components are reacted with one another under warm conditions.

Inventors

  • 👤 Heinz-Bernhard Hofel
  • 👤 Hans-Joachim Kiessling
  • 👤 Fred Lampert

Bibliographic Details

Application Number —
Jurisdiction US
Data Source google_patents
Last Synchronized 2026-10-28 18:42
CPC Classifications
C; C07; C07C; C07C37/00; C07C37/11; C07C37/14; C08; C08G; C08G8/00; C08G8/04; C08G8/08; C08G8/24; D; D06; D06M; D06M13/00; D06M13/10; D06M13/152; D21; D21H; D21H17/00; D21H17/20; D21H17/33; D21H17/46; D21H17/47; D21H17/48

Claims Analysis

Total Claims: 26
Claim 1
Independent Claim 23 words
PROCESS FOR THE MANUFACTURE OF A WATER-DILUTABLE, SELFEMULSIFIED, AQUEOUS DISPERSION OF A THERMOSETTING REACTION PRODUCT WHICH COMPRISES A. WARMING AN AQUEOUS MIXTURE OF
Claim 2
Dependent Claim 23 words
PROCESS FOR THE MANUFACTURE OF A WATER-DILUTABLE, SELFEMULSIFIED, AQUEOUS DISPERSION OF A THERMOSETTING REACTION PRODUCT WHICH COMPRISES A. WARMING AN AQUEOUS MIXTURE OF
Claim 3
Dependent Claim 1 words
PHENOL,
Claim 4
Dependent Claim 1 words
PHENOL,
Claim 5
Dependent Claim 49 words
A SUBSTITUTED PHENOL HAVING FROM 1 TO 14 SUBSTITUENTS ON THE PHENOL NUCLEUS AND HAVING AT LEAST ONE RING CARBON ATOM AVAILABLE FOR REACTION WITH FORMALDEHYDE, AND WHICH SUBSTITUTED PHENOL HAS A SPEED OF REACTION OF UNSUBIS 40 TO 150 PERCENT OF THE SPEED OF REACTION OF UNSUBSTITUTED PHENOL,
Claim 6
Dependent Claim 49 words
A SUBSTITUTED PHENOL HAVING FROM 1 TO 14 SUBSTITUENTS ON THE PHENOL NUCLEUS AND HAVING AT LEAST ONE RING CARBON ATOM AVAILABLE FOR REACTION WITH FORMALDEHYDE, AND WHICH SUBSTITUTED PHENOL HAS A SPEED OF REACTION OF UNSUBIS 40 TO 150 PERCENT OF THE SPEED OF REACTION OF UNSUBSTITUTED PHENOL,
Claim 7
Dependent Claim 49 words
a substituted phenol having from 1 to 4 substituents on the phenol nucleus and having at least one ring carbon atom available for reaction with formaldehyde, and which substituted phenol has a speed of reaction which is 40 to 150 percent of the speed of reaction of unsubstituted phenol,
Claim 8
Dependent Claim 49 words
a substituted phenol having from 1 to 4 substituents on the phenol nucleus and having at least one ring carbon atom available for reaction with formaldehyde, and which substituted phenol has a speed of reaction which is 40 to 150 percent of the speed of reaction of unsubstituted phenol,
Claim 9
Dependent Claim 76 words
Process of claim 1 wherein the substituted phenol component (2) is made by heating to about 150* to 160*C a mixture of phenol and a styrene compound in excess phenol as the solvent in the presence of from about 1 to 5 percent by weight of oxalic acid, relative to the total amount of phenol and the styrene compound, until the reaction mixture contains at least 95 percent by weight of an equimolar phenol-styrene reaction product.
Claim 10
Dependent Claim 57 words
Process of claim 1 wherein the substituted phenol (2) is selected from the group consisting of p-tert-butyl phenol o- Alpha -phenylethylphenol o- Beta -phenylethylphenol p- Alpha -phenylethylphenol p- Beta -phenylethylphenol o- Alpha -phenylisopropylphenol o- Beta -phenylisopropylphenol p- Alpha -phenylisopropylphenol p- Beta -phenylisopropylphenol o- Alpha -methylphenylethylphenol o- Beta -methylphenylethylphenol p- Alpha -methylphenylethylphenol p- Beta -methylphenylethylphenol, and mixtures thereof.
Claim 11
Dependent Claim 5 words
formaldehyde or a formaldehyde donor,
Claim 12
Dependent Claim 5 words
formaldehyde or a formaldehyde donor,
Claim 13
Dependent Claim 5 words
FORMALDEHYDE OR A FORMALDEHYDE DONOR,
Claim 14
Dependent Claim 5 words
FORMALDEHYDE OR A FORMALDEHYDE DONOR,
Claim 15
Dependent Claim 4 words
A SECONDARY AMINE, AND
Claim 16
Dependent Claim 4 words
A SECONDARY AMINE, AND
Claim 17
Dependent Claim 4 words
a secondary amine, and
Claim 18
Dependent Claim 4 words
a secondary amine, and
Claim 19
Dependent Claim 25 words
Process of claim 1 wherein as phenol (1) and substituted phenol (2) there is used a mixture of phenol and Alpha - and Beta -phenylethylphenol.
Claim 20
Dependent Claim 36 words
Process of claim 1 wherein a member of the group consisting of water, a protective colloid, and mixtures of water and a protective colloid are added to the mixture during the stirring and cooling step (b).
Claim 21
Dependent Claim 189 words
AN acid until a sample of the dispersion reaction mixture has a B-time of 30 seconds to 10 minutes at 160*C, and b. while stirring, cooling the mixture from step (a), said process being further characterized in the mixture of substituted phenol and phenol is employed in a ratio such that the average functionality of the sum of the phenolic compounds (1) and (2) relative to the formaldehyde component (3) is between 2.1 and 2.8, and the amount of formaldehyde in the mixture being so chosen that the molar ratio of the total sum of formaldehyde (3) to the sum of the phenolic compounds (1) and (2) ranges from about 0.9 to 1.5 to 1, and the secondary amine content (4) in the mixture ranges from about 50 to about 200 mol percent, relative to the total weight of the phenols (1) and (2), the amount of acid (5) in the mixture being equivalent to the secondary amine (4), the amount of water in the mixture, including added water and water of reaction, ranging from 30 to 60 percent by weight, relative to the weight of the total mixture.
Claim 22
Dependent Claim 189 words
AN acid until a sample of the dispersion reaction mixture has a B-time of 30 seconds to 10 minutes at 160*C, and b. while stirring, cooling the mixture from step (a), said process being further characterized in the mixture of substituted phenol and phenol is employed in a ratio such that the average functionality of the sum of the phenolic compounds (1) and (2) relative to the formaldehyde component (3) is between 2.1 and 2.8, and the amount of formaldehyde in the mixture being so chosen that the molar ratio of the total sum of formaldehyde (3) to the sum of the phenolic compounds (1) and (2) ranges from about 0.9 to 1.5 to 1, and the secondary amine content (4) in the mixture ranges from about 50 to about 200 mol percent, relative to the total weight of the phenols (1) and (2), the amount of acid (5) in the mixture being equivalent to the secondary amine (4), the amount of water in the mixture, including added water and water of reaction, ranging from 30 to 60 percent by weight, relative to the weight of the total mixture.
Claim 23
Dependent Claim 189 words
AN ACID UNTIL A SAMPLE OF THE DISPERSION REACTION MIXTURE HAS A B-TIME OF 30 SECONDS TO 10 MINUTES AT 160*C, AND B. WHILE STIRRING, COOLING THE MIXTURE FROM STEP (A), SAID PROCESS BEING FURTHER CHARACTERIZED IN THE MIXTURE OF SUBSTITUTED PHENOL AND PHENOL IS EMPLOYED IN A RATIO SUCH THAT THE AVERAGE FUNCTIONALITY OF THE SUM OF THE PHENOLIC COMPOUNDS (1) AND (2) RELATIVE TO THE FORMALDEHYDE COMPONENT (3) IS BETWEEN 2.1 AND 2.8, AND THE AMOUNT OF FORMALDEHYDE IN THE MIXTURE BEING SO CHOSEN THAT THE MOLAR RATIO OF THE TOTAL SUM OF FORMALDEHYDE (3) TO THE SUM OF THE PHENOLIC COMPOUNDS (1) AND (2) RANGES FROM ABOUT 0.9 TO 1.5 TO 1, FAND THE SECONDARY AMINE CONTENT (4), IN THE MIXTURE RANGES FROM ABOUT 50 TO ABOUT 200 MOL PERCENT, RELATIVE TO THE TOTAL WEIGHT OF THE PHENOLS (1) AND (2), THE AMOUNT OF ACID (5) IN THE MIXTURE BEING EQUIVALENT TO THE SECONDARY AMINE (4), THE AMOUNT OF WATER IN THE MIXTURE, INCLUDING ADDED WATER AND WATER OF REACTION, RANGING FROM 30 TO 60 PERCENT BY WEIGHT, RELATIVE TO THE WEIGHT OF THE TOTAL MIXTURE.
Claim 24
Dependent Claim 189 words
AN ACID UNTIL A SAMPLE OF THE DISPERSION REACTION MIXTURE HAS A B-TIME OF 30 SECONDS TO 10 MINUTES AT 160*C, AND B. WHILE STIRRING, COOLING THE MIXTURE FROM STEP (A), SAID PROCESS BEING FURTHER CHARACTERIZED IN THE MIXTURE OF SUBSTITUTED PHENOL AND PHENOL IS EMPLOYED IN A RATIO SUCH THAT THE AVERAGE FUNCTIONALITY OF THE SUM OF THE PHENOLIC COMPOUNDS (1) AND (2) RELATIVE TO THE FORMALDEHYDE COMPONENT (3) IS BETWEEN 2.1 AND 2.8, AND THE AMOUNT OF FORMALDEHYDE IN THE MIXTURE BEING SO CHOSEN THAT THE MOLAR RATIO OF THE TOTAL SUM OF FORMALDEHYDE (3) TO THE SUM OF THE PHENOLIC COMPOUNDS (1) AND (2) RANGES FROM ABOUT 0.9 TO 1.5 TO 1, FAND THE SECONDARY AMINE CONTENT (4), IN THE MIXTURE RANGES FROM ABOUT 50 TO ABOUT 200 MOL PERCENT, RELATIVE TO THE TOTAL WEIGHT OF THE PHENOLS (1) AND (2), THE AMOUNT OF ACID (5) IN THE MIXTURE BEING EQUIVALENT TO THE SECONDARY AMINE (4), THE AMOUNT OF WATER IN THE MIXTURE, INCLUDING ADDED WATER AND WATER OF REACTION, RANGING FROM 30 TO 60 PERCENT BY WEIGHT, RELATIVE TO THE WEIGHT OF THE TOTAL MIXTURE.
Claim 25
Dependent Claim 8 words
Product produced by the process of claim 1.
Claim 26
Dependent Claim 8 words
Product produced by the process of claim 2.

References Cited (Backward Citations)

US2482525A Cited
US2675335A Cited
US3351612A Cited
US3459128A Cited
US3770544A Cited
US3703494A Cited
US3761448A Cited
US3697482A Cited

USPTO Annuity & Maintenance Windows

Annuity Stage Window Opens Payment Deadline Surcharge Period Until Estimated Fee Status
3.5 Years (Year 4) 1978-04-14 1978-10-14 1979-04-15 $2000.00 Window Closed / Lapsed
7.5 Years (Year 8) 1982-04-14 1982-10-14 1983-04-15 $3760.00 Window Closed / Lapsed
11.5 Years (Year 12) 1986-04-14 1986-10-14 1987-04-15 $7700.00 Window Closed / Lapsed

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