GB2305670A - Hot melt ink jet vehicles - Google Patents
Hot melt ink jet vehicles Download PDFInfo
- Publication number
- GB2305670A GB2305670A GB9519646A GB9519646A GB2305670A GB 2305670 A GB2305670 A GB 2305670A GB 9519646 A GB9519646 A GB 9519646A GB 9519646 A GB9519646 A GB 9519646A GB 2305670 A GB2305670 A GB 2305670A
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- Prior art keywords
- acid
- material according
- hydroxy
- functional
- equivalent
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Classifications
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- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
- C09D11/00—Inks
- C09D11/30—Inkjet printing inks
- C09D11/34—Hot-melt inks
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C275/00—Derivatives of urea, i.e. compounds containing any of the groups, the nitrogen atoms not being part of nitro or nitroso groups
- C07C275/04—Derivatives of urea, i.e. compounds containing any of the groups, the nitrogen atoms not being part of nitro or nitroso groups having nitrogen atoms of urea groups bound to acyclic carbon atoms
- C07C275/06—Derivatives of urea, i.e. compounds containing any of the groups, the nitrogen atoms not being part of nitro or nitroso groups having nitrogen atoms of urea groups bound to acyclic carbon atoms of an acyclic and saturated carbon skeleton
- C07C275/14—Derivatives of urea, i.e. compounds containing any of the groups, the nitrogen atoms not being part of nitro or nitroso groups having nitrogen atoms of urea groups bound to acyclic carbon atoms of an acyclic and saturated carbon skeleton being further substituted by nitrogen atoms not being part of nitro or nitroso groups
Abstract
A hot melt ink jet vehicle is obtained by reacting a mono- or diisocyanate with one or more functional amide materials. The functional amides are the reaction products of one or more hydroxy functional primary or secondary amines and/or diprimary diamines together with a monofunctional carboxylic acid and/or hydroxy carboxylic acid and/or a difunctional carboxylic acid.
Description
HOT MELT INK JET VEHICLES
The present invention relates to the formulation of hot melt ink jet base materials (hereinafter referred to as "ink jet vehicles") with a view to improving their compatibility with viscosity modifying additives.
Ink jet printing generally comprises forming a patterned array of droplets of an ink upon a substrate to form the desired indicia on the substrate. In a hot melt ink jet printing process, the ink is one which is normally solid at ambient temperatures and which is applied to the substrate in molten form so that the droplets solidify on cooling on the substrate.
Typically, the ink employed in hot melt ink jet printing comprises a fusible carrier together with a colourant, i.e. a pigment or dyestuff.
Suitable materials for use as or in the vehicles for inks for hot melt ink jet printing (hereinafter, simply, "hot melt inks") should be relatively hard and non-tacky at ambient temperatures whilst being capable of melted to form inks. Suitably, they have a melting point of at least 65"C.
Patent Specification WO 94/14902 describes the use of certain urethane oligomers as hot melt ink vehicles. These oligomers are the reaction products of diisocyanates with a monohydric alcohol component, optionally followed by another monohydric component or a dihydric alcohol component followed by a monohydric alcohol component. These materials have melting points in excess of 650C, low melt viscosities and good colour and viscosity stabilities at elevated temperatures. However, they are compatible with only a limited number of viscosity modifiers.
This drawback may limit the range of applications of such materials, where certain specific properties, not possessed by the materials alone, are required.
A new class of hot melt ink jet vehicles has now been devised, which overcomes the aforementioned limitation in the range of possible applications. Thus, in accordance with the present invention, there may be used as hot melt ink jet vehicles, the reaction products of a mono- or diisocyanate and one or more difunctional amides. The present invention also provides the use of a urea or urethane compound having a melting point greater than 65"C, as a hot melt ink jet vehicle, the urea or urethane compound being the reaction product of a mono- or diisocyanate and a difunctional amide.
According to one embodiment of the present invention, there is provided a material suitable for use in a hot melt ink, the material being obtainable by reacting a mono- or diisocyanate with one or more functional amide materials which are the reaction products of:
(a) (i) one or more hydroxy difunctional primary or secondary
amines; or
(ii) one or more diprimary diarnines; or
(iii) a mixture of components (i) and (ii); and
(b) a monofunctional carboxylic acid, a hydroxy carboxylic acid
or difunctional carboxylic acid or a mixture of any two or more thereof.
Very preferably, materials according to the present invention have a a melting point in excess of 650C. They also have good thermal colour and viscosity stability as well as improved compatibility with common viscosity modifiers.
More specifically, preferred materials according to the present invention may be produced by reacting a mono- or di-functional aliphatic or aromatic isocyanate with an at least stoichiometric amount of:
(i) the reaction product of one equivalent of a diprimary diamine component with one equivalent of a monocarboxylic acid and one equivalent of a hydroxy functional monocarboxylic acid;
(ii) the reaction product of one equivalent of a diprimary diamine component with one equivalent of a monocarboxylic acid;
(iii) the reaction product of one equivalent of a primary monoamine with hydroxy functionaiity, with one equivalent of a monocarboxylic acid; or
(iv) the reaction products (i) or (ii), but where an equivalent of acid functionality is made up of a proportion of monocarboxylic acid, dicarboxylic acid and/or hydroxy functional monocarboxylic acids.
The amides produced by the reactions described above may be hydroxy or amine functional, depending on the proportions and type of reagent used. Thus the reaction products obtained from these amides and the isocyanate materials will be urethane or urea compounds depending on whether the isocyanate groups react with hydroxy or amine groups respectively.
As noted above, it is greatly preferred that materials according to the present invention (hereinafter referred to as urethane-amides or ureaamides) have a melting point greater than 650C (as determined by the ball and ring method). It should be noted that not all materials obtainable by the processes outlined above have melting points greater than 650C. Our experiments have shown that there is a wide range of melting points and that attempts to predict the melting point, by taking molecular weight or component reagents into account, are fruitless. However, of course it is simple to measure the melting point once the material has been made, by simple routine and trial.
Suitable isocyanates for use in the preparation of the urethane- and urea-amides include octadecylmonoisocyanate, toluene diisocyanate, diphenylmethane-4,4'-diisocyanate (MDI), hexamethylene-1,6- diisocyanate, naphthalene-1,5 diisocyanate, 3,3 '-dimethyl-4,4'-biphenyl diisocyanate, isophorone diisocyanate, trimethylhexamethylene diisocyanate and tetramethylene xylene diisocyanate. Of these isocyanates the aliphatic materials are generally preferred to the aromatic ones for reasons of heat and viscosity stability. In particular isophorone diisocyanate, trimethylhexamethylene diisocyanate and octadecyl monoisocyanate have been found to be particularly suitable for this application.
Diprimary diamines which may be used to produce the amides for isocyanate adduction, including ethylene diamine, neopentane diamine, 2,4,4-trimethylhexandiamine, 2-butyl-2-ethyl 1,5 pentane diamine, 1,3diaminopentane, isophorone diamine and 2 methyl 1,5 pentamethylene diamine. Hydroxy functional primary and secondary amines which may be used are ethanolamine, diethanolamine and n-methyl diethanolamine. In particular ethylene diamine is suitable in this type of formulation.
Monocarboxylic acids which are suitable for this application are stearic acid, acetic acid, 3,5,5-trimethylhexanoic acid, decanoic acid, propanoic, acid 2,2 dimethyl propionic acid, isooctanoic acid, isoheptanoic acid, isobutynic acid, or isodecanoic acid. Stearic and 3,5,5trimethylhexanoic acids have proved particularly suitable in this application. Dimer acids are suitable difunctional carboxylic acids.
Hydroxy functional monocarboxylic acids which may be used include 12-hydroxy stearic acid, 1 2-hydroxydodecanoic acid, 2hydroxyhexanoic acid, 1 6-hydroxyhexadecanoic acid and 2hydroxyisobutyric acid. 1 2-hydroxystearic acid and 12hydroxydodecanoic acid have proved particularly useful in this application.
The amide components of the hot melt ink vehicle typically have melting points (ball and ring) of > 50 C and viscosities < 200 centipoise at 1250C.
The condensation reaction used to produce the amide component of the urethane- and urea-amides proceeds without need of a catalyst. The reaction of the amide with the isocyanate component may also be carried out without a catalyst, but catalysts such as dibutyl tin dilaurate and stannous octoate may be used to ensure full reaction of the isocyanate fraction.
The final average molecular weight of the urethane- or urea-amides is typically from 400 to 2000, preferably from 800 to 1400. These materials having melting points of from room temperature (e.g. 20"C) to 1300C and melt viscosities of from 10 to 800 centipoise at 1250C.
For some applications of hot melt inks it is advantageous if the urethane- or urea-amides are transparent. As with the melting points described previously, it is impossible to predict which particular mix of reagents will produce a clear product. Again determination of suitable materials is by simple trial and experiment. Similarly, the viscosity of the materials at elevated temperatures is not easily predicted, materials with viscosities lower than 200 centipoise at 1250C proving of greatest use for this type of application, with materials with viscosities less than 50 centipoise at 125"C being of particular interest.
The urea- and urethane-amides of this invention are used as vehicles, or as a components of vehicles, of hot melt ink jet inks. As well as the aforementioned urea- and urethane-amides these inks will also contain pigments or dyes, viscosity modifying additives and antioxidants.
Generally the vehicle (urea- or urethane-amide) will make up 50-95% by weight, especially 75-95% by weight of any ink, with viscosity modifying additives making up the bulk of the remainder and other additives, such as antioxidants, pigments, dyes, etc. in small amounts to make up the balance, e.g. typically less than 10% by weight of the total formulation.
Materials which may typically be used to modify the viscosity of inks containing the urea- or urethane-amides are; stearone, carnauba wax, stearyl stearamide, hydrogenated castor oil and erucamide.
The compatibility of the materials with dye stuffs and pigments must be determined by experimentation, but most of the colorants commonly used in ink jet applications are suitable.
The present invention will now be explained in more detail by way of the following non-limiting examples.
Example An amine functional amide material was prepared by reacting one mole of ethylene diamine with one mole of stearic acid. When fully processed this amide material had an acid value of 2.5 mg KOH/g and an amine value of 69.5 mg KOH/g. The ball and ring melting point of the material was 1280C and it had a viscosity of < 10 centipoise at 1500C.
This material was designated amide 1.
Example 2
An amine functional amide material was prepared by one mole of ethylene diamine with one mole of 3,5,5-trimethylhexanoic acid. The resulting amide material had a ball and ring melting point of 520C and a viscosity of < 10 centipoise at 125"C. The acid value of the material was 4.2 mg KOH/g and its amine value was 125.4 mg KOHlg. This material was designated amide 2.
Example 3
An amine functional amide material was prepared by reacting one mole of isophorone diamine with one mole of stearic acid. The resultant solid had an acid value of 1.2 mg KOH/g and an amine value of 117.0 mg
KOH/g. Its melting point by the ball and ring method was 610C and at 125"C its viscosity was less than 10 centipoise. This material was designated amide 3.
Example4 A hydroxy functional amide material was prepared by reacting one mole of ethylene diamine with one of 12-hydroxystearic acid and one mole of 3,5,5-trimethylhexanoic acid. The opaque solid produced had a hydroxy value of 109.1 mg KOH/g, an acid value of 7.5 mg KOH/g and an amine value of 9.0 mg KOH/g. The diamide had a ball and ring melting point of 129"C and a viscosity at 125"C of 50 centipoise. This material was designated amide 4.
Example 5
Trimethylhexamethylene diisocyanate (1 mole) was charged to a round bottomed reaction flask fitted with a stirrer, a thermometer and an inert gas (nitrogen) sparge line. The material was heated to 600C and amide 1(2 moles) added carefully to it, such that the temperature of the resultant exotherm did not climb above 1000C. When all of the amide had been added and no further exotherm was observed, the reaction was heated to 1 500C and held until the free isocyanate content of the ureaamide formed was below 30 ppm (as determined by titration and IR analysis).
This reaction yielded an opaque solid urea-amide with a ball and ring melting point of 1280C, a softening point of 1360C (as determined by differential scanning calorimetry) and a viscosity of less than 10 centipoise at 1500C.
Example6 Octadecyl isocyanate (1 mole) was charged into a flask and was heated with stirring and under an inert atmosphere to 850C. Amide 2(1 mole) was then carefully added in powdered form at a rate which prevented the resultant exotherm from climbing about 1000C. Once all the amide had been added and the exothenn had abated, the reaction was driven to completion by heating it to 1600C.
this reaction produced an urea-amide material with a ball and ring melting point of 940C, a DSC determined softening point of 73.4"C, a free isocyanate content below 30 ppm and a viscosity of 30 centipoise at 1250C.
ExamDle 7
Octadecyl isocyanate (1 mole) was charged to a flask and heated to 600C with stirring and under an inert atmosphere. Amide 3 (1 mole) was carefully added to the reaction flask at a rate such that the temperature of reaction did not climb above 1000C. When the reaction no longer exothermed, it was heated up to 1500C and controlled at this temperature until the free isocyanate value had dropped down below 30 ppm
The batch was then cooled and discharged to yield a translucent, solid urea-amide with a ball and ring melting point of 630C, a DSC determined softening point of 430C and a viscosity of 220 centipoise at 125"C.
Example 8 Trimethylhexamethylene isocyanate (1 mole) and octadecyl isocyanate (1 mole) were charged to a heated flask and heated under a nitrogen atmosphere and under stirring to 650C. Amide 4(3 moles) was then carefully added to the mixture of isocyanates, ensuring that the reaction temperature did not climb above 100"C. Once all the amide had been added and all exothenning had ceased, the batch was slowly heated up to 1600C and held at this temperature until the isocyanate content had dropped below 30 ppm.
The resulting solid urethane-amide was a clear material with a ball and ring melting point of 950C, a DSC determined softening point of 710C and a viscosity of 150 centipoise at 1250C.
Claims (17)
1. A material suitable for use in a hot melt ink, the material being obtainable by reacting a mono- or diisocyanate with one or more functional amide materials which are the reaction products of:
(a) (i) one or more hydroxy functional primary or secondary
amines; or
(ii) one or more diprimary diamines; or
(iii) a mixture of components (i) and (ii); and
(b) a monofunctional carboxylic acid, a difunctional carboxylic
acid or a hydroxy carboxylic acid or a mixture of any two
or more thereof.
2. A material according to claim 1, wherein functional amide material(s) is or are selected from:
(i) the reaction product of one equivalent of a diprimary diamine component with one equivalent of a monocarboxylic acid or hydroxy functional monocarboxylic acid;
(ii) the reaction product of one equivalent of a diprimary diamine component with one equivalent of a monocarboxylic acid;
(iii) the reaction product of one equivalent of a primary monoamine with hydroxy functionality, with one equivalent of a monocarboxylic acid; or
(iv) the reaction products (i) or (ii), but where an equivalent of acid functionality is made up of a proportion of monocarboxylic acid, dicarboxylic acid and/or hydroxy functional monocarboxylic acids.
3. A material according to either preceding claim, wherein the functional amide has hydroxy functionality and the resultant material is a urethane compound.
4. A material according to claim 1 or claim 2, wherein the functional amide has amine functionality and the resultant material is a urea compound.
5. A material according to any preceding claim, wherein the mono- or diisocyanate is aliphatic.
6. A material according to claim 4, wherein the mono- or diisocyanate is selected from isophorone diisocyanate, trimethylhexamethylene diisocyanate and octadecyl monoisocyanate.
7. A material according to any preceding claim, wherein the at least one said functional amide material is produced from a diprimary diamine selected from ethylene diamine, neopentane diamine, 2,4,4trimethylhexandiamine, 2-butyl-2-ethyl 1,5 pentane diamine, 1,3diaminopentane, isophorone diamine and 2 methyl 1,5 pentamethylene diamene.
8. A material according to any preceding claim, wherein the at least one said functional amide material is produced from a hydroxyfunctional primary or secondary amine selected from ethanolamine, diethanolamine and n-methyl diethanolamine.
9. A material according to any preceding claim, wherein the at least one said functional amide material is produced from a monofunctional carboxylic acid selected from stearic acid, acetic acid, 3,5,5trimethylhexanoic acid, decanoic acid, propanoic acid, 2,2 dimethylpropionic acid, isooctanoic acid, isoheptanoic acid, isobutyric acid and isodecanoic acid.
10. A material according to any preceding claim, wherein the at least one said functional amide material is produced from a hydroxy carboxylic acid selected from 12-hydroxy stearic acid, 1 2-hydroxydodecanoic acid, 2hydroxyhexanoic acid, 16-hydroxyhecadecanoic acid and 2hydroxyisobutyric acid.
11. A material according to any preceding claim, having a melting point greater than 65"C.
12. A material according to any preceding claim, wherein the functional amide material has a melting point greater than 50"C and a viscosity less than 200 centipoise at 125"C.
13. A material according to any preceding claim, having an average molecular weight of from 400 to 2000.
14. A material according to any preceding claim, having a melting point of from 20"C to 1300C and a melt viscosity of from 10 to 800 centipoise at 125"C.
15. A material for use in a hot melt ink, the material being substantially as hereinbefore described with reference to any of Examples 5 to 8.
16. A hot melt ink comprising a colourant and a material according to any preceding claim
17. A hot melt ink according to claim 15, further comprising a viscosity modifier.
Priority Applications (6)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
GB9519646A GB2305670A (en) | 1995-09-27 | 1995-09-27 | Hot melt ink jet vehicles |
PCT/GB1996/002399 WO1997012003A1 (en) | 1995-09-27 | 1996-09-27 | Hot melt ink jet vehicles |
EP96932687A EP0852608B1 (en) | 1995-09-27 | 1996-09-27 | Hot melt ink jet vehicles |
AU71374/96A AU7137496A (en) | 1995-09-27 | 1996-09-27 | Hot melt ink jet vehicles |
US09/043,799 US6255432B1 (en) | 1995-09-27 | 1996-09-27 | Hot melt ink jet vehicles |
DE69632636T DE69632636T2 (en) | 1995-09-27 | 1996-09-27 | MELTABLE INK MEDIA FOR INK JET PROCESSING |
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
GB9519646A GB2305670A (en) | 1995-09-27 | 1995-09-27 | Hot melt ink jet vehicles |
Publications (2)
Publication Number | Publication Date |
---|---|
GB9519646D0 GB9519646D0 (en) | 1995-11-29 |
GB2305670A true GB2305670A (en) | 1997-04-16 |
Family
ID=10781313
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
GB9519646A Withdrawn GB2305670A (en) | 1995-09-27 | 1995-09-27 | Hot melt ink jet vehicles |
Country Status (6)
Country | Link |
---|---|
US (1) | US6255432B1 (en) |
EP (1) | EP0852608B1 (en) |
AU (1) | AU7137496A (en) |
DE (1) | DE69632636T2 (en) |
GB (1) | GB2305670A (en) |
WO (1) | WO1997012003A1 (en) |
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Family Cites Families (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JPH0730279B2 (en) * | 1990-11-21 | 1995-04-05 | 三洋化成工業株式会社 | Binder for printing ink |
JPH04261477A (en) * | 1991-02-15 | 1992-09-17 | Canon Inc | Recording medium which is solid at ordinary temperature and method for recording |
GB9226772D0 (en) * | 1992-12-23 | 1993-02-17 | Coates Brothers Plc | Hot melt ink jet printing |
-
1995
- 1995-09-27 GB GB9519646A patent/GB2305670A/en not_active Withdrawn
-
1996
- 1996-09-27 US US09/043,799 patent/US6255432B1/en not_active Expired - Fee Related
- 1996-09-27 WO PCT/GB1996/002399 patent/WO1997012003A1/en active IP Right Grant
- 1996-09-27 DE DE69632636T patent/DE69632636T2/en not_active Expired - Fee Related
- 1996-09-27 EP EP96932687A patent/EP0852608B1/en not_active Expired - Lifetime
- 1996-09-27 AU AU71374/96A patent/AU7137496A/en not_active Abandoned
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Also Published As
Publication number | Publication date |
---|---|
EP0852608A1 (en) | 1998-07-15 |
DE69632636D1 (en) | 2004-07-08 |
AU7137496A (en) | 1997-04-17 |
US6255432B1 (en) | 2001-07-03 |
EP0852608B1 (en) | 2004-06-02 |
DE69632636T2 (en) | 2005-05-25 |
WO1997012003A1 (en) | 1997-04-03 |
GB9519646D0 (en) | 1995-11-29 |
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