IE903092A1 - Process for the stabilization of chlorinated paraffins - Google Patents
Process for the stabilization of chlorinated paraffinsInfo
- Publication number
- IE903092A1 IE903092A1 IE309290A IE309290A IE903092A1 IE 903092 A1 IE903092 A1 IE 903092A1 IE 309290 A IE309290 A IE 309290A IE 309290 A IE309290 A IE 309290A IE 903092 A1 IE903092 A1 IE 903092A1
- Authority
- IE
- Ireland
- Prior art keywords
- chlorinated
- fatty amine
- paraffin
- weight
- essentially straight
- Prior art date
Links
Classifications
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B41—PRINTING; LINING MACHINES; TYPEWRITERS; STAMPS
- B41M—PRINTING, DUPLICATING, MARKING, OR COPYING PROCESSES; COLOUR PRINTING
- B41M5/00—Duplicating or marking methods; Sheet materials for use therein
- B41M5/124—Duplicating or marking methods; Sheet materials for use therein using pressure to make a masked colour visible, e.g. to make a coloured support visible, to create an opaque or transparent pattern, or to form colour by uniting colour-forming components
- B41M5/165—Duplicating or marking methods; Sheet materials for use therein using pressure to make a masked colour visible, e.g. to make a coloured support visible, to create an opaque or transparent pattern, or to form colour by uniting colour-forming components characterised by the use of microcapsules; Special solvents for incorporating the ingredients
- B41M5/1655—Solvents
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C17/00—Preparation of halogenated hydrocarbons
- C07C17/38—Separation; Purification; Stabilisation; Use of additives
- C07C17/42—Use of additives, e.g. for stabilisation
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Heat Sensitive Colour Forming Recording (AREA)
Abstract
Chlorinated paraffins which contain fatty amine oxyethylates as stabilisers are outstandingly suitable as solvents for the colour formers in chemically reacting copying papers.
Description
Process for the stabilization of chlorinated paraffins
The invention relates to the stabilization of chloro5 paraffins which are used as solvents for the colorforming agents of chemically reacting transfer copying papers.
Most carbon-free transfer copying papers used today operate by the principle of color formation by reaction of an electron-donating organic compound, the so-called color-forming agent, which has only an exceptionally low intrinsic color, if any, with an electron-accepting substance, the so-called color developer.
The usual pressure-sensitive copying papers consist of a combination of a top sheet of paper, to the back of which the microencapsulated emulsion of the color-forming agent is applied (donor layer = CB layer = coated back). The electron-accepting substance for the color development is applied to the undersheet of paper (acceptor layer = CF layer = coated front). A transfer copying set having three or more sheets operates with intermediate sheets which carry the CF layer on the top side and the CB layer on the under-side (CFB intermediate sheets).
The microcapsules in which the dissolved color-forming agent is enclosed are destroyed by pressure or impact and the color-forming agent solution is absorbed and fixed immediately by the absorbent acceptor layer.
Electron-accepting substances or colors developers for the CF layer which are known are:
- acid-activated layered aluminum silicates based on montmorillonite, activated clay grades, such as, for example, silton, bentonites, attapulgites or synthetic products, such as, for example, treated cates specific zinc salicylate compounds phenolic resins, such as, for example, condensation products of para-phenylphenol or para-alkylphenols with formaldehyde.
Examples of color-forming agents which are used for the CB layer are crystal violet lactone, malachite green lactone, benzoyl-leucomethylene blue, rhodamine B lactone and similar substances. A mixture of different color10 forming agents is employed in most cases.
Many organic liquids can be used as solvents for the color-forming agents, the customary substances being modified terphenyls or alkylated naphthalenes or diphenyls in combination with various types of kerosine.
The use of straight-chain chlorinated paraffin hydrocarbons having 6 to 18 carbon atoms and chlorine contents of 20 to 60% by weight as solvents for the color-forming agents is known (cf. British patent 1,296,477). Chloroparaffins have the desired properties imposed on the solvent. They are good solvents for the color-forming agents and they are available in all classes of viscosity by appropriate variation of the carbon chain lengths of the paraffins and of the degree of chlorination. They have no troublesome smell. Chlorinated paraffins do not reduce the sensitivity of the CF layer to color formation.
However, it has been found that stabilization using the epoxidized oils, for example epoxidized soyabean oil or resins containing epoxide groups, which are usually employed in chlorinated paraffins is not sufficient, using these compounds by themselves, to prevent color formation in the color-forming agent solution even at room temperature. This effect manifests itself by fogging on the transfer copying papers, this being intensified further by elevated temperature or under sunlight. The intensity of the written image also suffers from this undesirable color formation.
The object was therefore to discover a stabilization which does not have the abovementioned disadvantages.
It has been found that premature discoloration of the color-forming agent solution can be prevented by addition of certain fatty amine ethoxylates to the chlorinated paraffin.
The invention thus relates to a process for the 10 stabilization of a chlorinated, essentially straightchain paraffin having 7 to 35 carbon atoms and a chlorine content of 10 to 72% by weight, which comprises adding to the chlorinated paraffin 0.1 to 3% by weight, based on the chlorinated paraffin, of at least one fatty amine oxyethylate.
The invention furthermore relates to a chlorinated essentially straight-chain paraffin having 7 to 35 carbon atoms and a chlorine content of 10 to 72% by weight and containing 0.1 to 3% by weight, based on the chlorinated paraffin, of at least one fatty amine oxyethylate, and to its use.
The chlorinated paraffins to be stabilized according to the invention are chlorination products of essentially straight-chain paraffins having 7 to 35 carbon atoms in the molecule, preferably of industrial paraffin cuts having, for example, 10 to 13, 14 to 17, 18 to 24 and so on carbon atoms. The chlorine contents of these chlorination products is 10 to about 72% by weight.
The fatty amine oxyethylates to be used according to the invention are obtained by the action of ethylene oxide on fatty amines. The reaction can be simplified in summary form by the following equation:
- 4 R-CH2-NH2 + 2n H2C-pH2
R - CH2 - N= £( CH2 CH2 0) πη] ,
Fatty amine Ethylene oxide Fatty amine oxyethylate 2n = number of molecules of ethylene oxide added on.
Structurally dihydric alcohols having terminal hydroxyl groups are formed from the fatty amines by adding on ethylene oxide. Fatty amine ethoxylates are basic in nature and give an alkaline reaction in aqueous solution. Their physico-chemical properties, in particular the surface-active properties, are determined decisively by the ratio of hydrophobic fatty amine radicals to hydro10 philic polyglycol chains in the total molecule. The length of the polyglycol chain is determined by the number of molecules of ethylene oxide added on per molecule of fatty amine. Since both the nature of the fatty amine and the amount of ethylene oxide can be chosen as desired, there are many possibilities for modifying the hydrophilic/lipophilic equilibrium.
Preferred fatty amines are:
coconut fatty amine - saturated C8-C16-fatty amines, predominantly C12-C1A;
stearylamine - unsaturated C16-C18-fatty amines;
oleylamine - predominantly unsaturated C18-fatty amine; tallow fatty amine - predominantly unsaturated C16-C20fatty amine.
The number of molecules of ethylene oxide added on is 2 to 25, preferably 2 to 25 molecules of ethylene oxide per molecule of fatty amine. The fatty amine oxyethylates are more water-soluble or more soluble in hydrocarbons or chlorinated paraffins, depending on the fatty amine used and the number of ethylene oxide molecules (degree of oxyethylation).
The chlorinated paraffin contains the fatty amine oxyethylate in an amount of 0.1 to 3, preferably 0.5 to 2% by weight, based on the chlorinated paraffin.
The chlorinated paraffin used can additionally also 5 contain the known stabilizers, for example epoxidized oils, such as epoxidized soyabean oil, or epoxidized resins, for example cycloaliphatic diepoxide, in an amount of 1 to 4% by weight. Stabilization with a combination of cycloaliphatic glycidyl esters with tertiary esters of phosphorous acid is also possible.
The chlorinated paraffin is advantageously stabilized immediately when the chlorination has ended, by incorporation of the stabilizer or stabilizers into the still warm chlorination product. Optimum degrees of stability are achieved in this way.
As solvents for the color-forming agents, chlorinated paraffins stabilized in this way result in no fogging of the transfer copying papers produced with them. The fatty amine oxyethylates furthermore have the effect of a good dispersibility of the color-forming agent solution in water because of their surface-active properties. As a result of the good solubility of the fatty amine oxyethylates in chlorinated paraffins, no additional solubilizing agents are necessary. The addition of surfactants can likewise be dispensed with because of the surface-active properties of the fatty amine oxyethylates. Fatty amine oxyethylates therefore combine a number of properties in one substance and thus provide a considerable advance.
As is usually customary in practice, the chlorinated paraffins stabilized according to the invention can be mixed with another solvent, for example with a hydrocarbon diluent, for example a kerosine grade.
The invention is illustrated in more detail in the examples which follow.
- 6 Examples
0.2 g of color-forming agent - crystal violet lactone was dissolved in 100 g portions of chlorinated paraffin stabilized with fatty amine oxyethylates. This solution was heated at 120°C over a period of 80 minutes. Samples were taken at intervals of time of 10, 15, 20, 30, 40, 50, 60 and 80 minutes and were rapidily cooled to room temperature, and the optical density - absorption of light - of the sample was measured on a spectrophotometer at 605 nm in a 1 cm cell against a blank sample of the same chlorinated paraffin type which contained fatty amine oxyethylate but no color-forming agent and had been heated under the same conditions. At the end of the experimental period of 80 minutes, the iodine color number of the color-forming agent solution was also measured to determine the ageing of the chlorinated paraffin.
The following chlorinated paraffins were employed:
A: chlorinated, essentially straight-chain paraffin having 14-17 carbon atoms and a chlorine content of about 52% by weight, commercial product.
B: chlorinated, essentially straight-chain paraffin having 14-17 carbon atoms and a chlorine content of about 40% by weight, commercial product.
C: chlorinated, essentially straight-chain paraffin having 14-17 carbon atoms and a chlorine content of about 50% by weight.
D: chlorinated, essentially straight-chain paraffin having 10-13 carbon atoms and a chlorine content of about 40% by weight.
E: chlorinated, essentially straight-chain paraffin having 10-13 carbon atoms and a chlorine content of about 40% by weight.
Fs chlorinated, essentially straight-chain paraffin having 14-17 carbon atoms and a chlorine content of about 50% by weight.
The chlorinated paraffins were stabilized with an epoxidized soyabean oil or a cycloaliphatic diepoxide. The fatty amine oxyethylates used were of the coconut fatty amine oxyethylate, stearylamine oxyethylate, oleylamine oxyethylate and tallow fatty amine oxyethylate type having 8 to 25 molecules of ethylene oxide per molecule of fatty amine. The results obtained are summarized in Tables 1 - 6. The figures quoted for each of the fatty amine oxyethylates in the Tables indicate the number of molecules of ethylene oxide per molecule of fatty amine.
β ftP in
Φ
P id >1
Λ
P
0)
S’
CD
C •d ►i
P
P id fo •d
O id td o
to
Table a
CD
N •d
Ό •d
X
Φ o
ftp m
Φ ft
P c
•d
H-l
H-l id
M id
Ό
Φ
P id c
•d d
O id
Λ o
o c
d o
ι—I 0 u
Φ c
•d
Ό
O
O C 00 O •d
P 04 o d vo 0 co
Λ id o v
fiP c
•d td
P •d o o o o CN CN CN CN in cn id in o
P id in oo VO cn oo σ> vo in cn o
CN id in Id id o
•d
P 04 o O «d vo tn cn cn
V CN cn o
CN in o m ο o •d id id CN id
ΓIO Cao vo ιο vo
CN CN
O ld O ld o CN vo o o o
d id I id eh
Φ id Ρ Φ Id >d id O £
P φ id
S’ &
o id Φ
Φ P ο ω •d id
P
P id fo p
υ o
o
CN O id CN cn cn
O -d d cn
O id o in oo m
- 9 04
Table dP in
Φ +J <0 r-4 £
4-)
0)
Φ
C •H +4
4->
(0 fa i-4 •<-t (0 >1
O (0
TJ
Φ
N •H
Ό •H
X
O
CU
Φ dP in
CQ ··
Φ ft
4J
C •H <0
H <0 ft
Ό
Φ
4->
Ci •H n
o r-4
X o
o
Ci
H i—l o
ϋ
Φ c
•H
Ό
H
O C oo O •H
4J ft O (4 VO 0 n
Λ <β ο dP
C ' •Η O tn >4 +J •r4 (Q O C 04 Φ Ό
-ι in (Q i-4 U H
4-) ft O O
IQ
Eh i—I
Φ S 4-) Φ <0 r-4 ι-Ι O >4 Λ 4->
Φ ι—I fc ft
O IQ Φ
Φ 4-) β W •H
4J
4J <0 fa
P c
ϋ
U inomoooinininin i-4 i—t 1—4 i—4 I—4 i“4 r—I ι—I ι—Ii—I inr*iO4*
I— ointnt'JCMf'Jtn^'mM' r*
04 04 io ι-l i-l i-4 04 04 04 CO Ή Π i-4 1-4 ι-H Γ4
O-OOOOOOr-IO m
mooooooooo r^ooooooooo
04 o i-4 04 o in oo m cn
Table
- 10 <*>
m
Φ +J (β ι-1
S
Λ
P
0) p
p (fl
Pm
C •H (0
Φ
P
Ό
Φ
N •rl
Ό •r|
X
CM
Φ dp
Φ e
p
CS •H
M-l
MM (fl
P (fl
CM
Ό Φ P (fl C •H l-i 0 ι—I Λ O
O
C
P
O ι—I 0 u
Φ c
•p
Ό o C 00 0 •P
P CM O P M3 O n
Λ <0 © «t dP ts •r| O tn >1 +J •H ra ©
C CN
Φ
Ό i-ι in (fl «—ι u •r|
P ' CM © Ο ή
Φ
P (fl
Φ c
•rl >1
P
P (fl
CM (fl >1
Φ ι—I O &
(fl
Φ
P
M
P il «3
O u
u ©©OOOCNOOO©
CN I—I CN CN CN rM rd ι-H rH I—I
ΟίυσισΊΐη’ίίοιηωιο r* co
Ocn^<«e<
CO in
(n·—Ii—(ι—(ι—(©©©ΟΉ cn
Oi-HOrHOOOOOi-l
CN
COOOOOOOOOiH ι cn © o in
CN O •-I CN oo m
Table dP m
Φ
P
P <0
IP •P o
(fl >1
N •P σ
Ή
X ο
CL φ
ο dp m
φ &
Ρ c
•Η
Ή
Ή ιβ
Ρ «0
Οι
Ό
Φ
Ρ ιβ
Ο •Η
Ρ ο
>Ρ
Λ
U
Ο
C5
Ρ
Ο ιΡ
Ο
U
Φ
C
Μ ύ
ο
Η
C
Ο •Ρ
Ρ
Οι
Ρ
Ο (0 <0 <*>
Ο •Ρ >1
Ρ •Ρ to ο
φ
Ό (β
U
Ρ
Ρ
Οι
Ο φ
Ρ φ
ιΡ £
Ρ φ
ο φ
ο •Ρ
Ρ
Ρ
κ) (Ρ ιη ο
ο ιη ο
Ρ* ο
CXJ ιη
Ιβ
Ε-ι >Ρ >1 φ
ιΡ ο
&
(β φ
Ρ (0
Ρ ο
ο υ
ο υ
m m οο ο CN οο ο ο ιη
CN ο •Ρ·
I ο
CN
I >1
Table dp m
Φ
4-) ia
4-)
Φ o
Φ cj >·.
4J
4-) <0
Em n
Φ
M
Ό
Φ
N •H
Ό •H
X o
dP ··
(0 <0
O4
Ό
Φ
4-) (0
C •r| u
r-l
Λ
U o
c n
o r-l o
u
Φ c
•H
Ό
O
M o C oo O H
4-> ft O h io 0 co
Λ ' (0 o
Ί· dP
C •Η O ro >.
4->
•d I» O
Ό —ι in (0 Ή u •H +J ft © O <0
Fi
Φ
4-) (0 +J
Φ
4-)
4-1 «0
Cm >1 &
(0
Φ
4J n
c o
u
O PO in ή oo
CO r-l 00 r-l O r* o in o
tN σι o
I O rs >4
- 13 C£>
Table dP in
Φ +j id £
+j
a) c
•H >1 +J +J id b
c •H (0
Φ
H
Ό
Φ
N
Ό ••H
X a
φ o
<*>
in
O c
M O ι—I o
u
Φ c
•r|
Ό
O o C oo O •H +J CU O W IO 0 to
Λ id o
M· dP ti ' •rl O m
+J •rl CO o C CN Φ Ό rH in Id rH υ •r| +J CU o O rH id
Eh
Φ
Φ 4-1 4J Φ id rH c •H o •H >1 MH X! MH 4J
Φ
S’ &
id
U id
cu 0 id φ Ό Φ +j Φ a ω 4J •H id g c 3 4-> •r| 3 H >H ti O +J 0 rH 4-> u x: id 0 o b u
Ο O
O CN CN O CN oorHoor-r^mr^r-uDr^ 00 rH cooomH'^n^^m^· oo
Cn^CNOrHrHrHrHrHrH
Γ
P'CNrHOOrHrHOrHO m
CNrHrHOOOOOOO r-'ooooooooo
CN
CMOOOOOOOOO o in
CN O rH CN in
I in o
HOE 89/F 281
Claims (10)
1. A process for the stabilization of a chlorinated, essentially straight-chain paraffin having 7 to 35 carbon atoms and a chlorine content of 10 to 72% by weight, 5 which comprises adding to the chlorinated paraffin 0.1 to 3% by weight, based on the chlorinated paraffin, of at least one fatty amine oxyethylate.
2. The process as claimed in claim 1, wherein the fatty amine oxyethylate is based on coconut fatty amine, 10 stearylamine, oleylamine or tallow fatty amine.
3. The process as claimed in claim 1, wherein the fatty amine oxyethylate is a reaction product of in each case 1 mol of fatty amine with 2 to 30 mol of ethylene oxide.
4. The process as claimed in claim 1, wherein 1 to 4% by 15 weight, based on the chlorinated paraffin, of an epoxide stabilizer is additionally added to the chlorinated paraffin.
5. A chlorinated, essentially straight-chain paraffin having 7 to 35 carbon atoms and a chlorine content of 10 20 to 72% by weight and containing 0.1 to 3% by weight, based on the chlorinated paraffin, of at least one fatty amine oxyethylate.
6. The use of a chlorinated paraffin as claimed in claim 5 for the production of chemically reacting transfer 25 copying papers.
7. A process according to claim 1 for the stabilization of a chlorinated, essentially straight-chain paraffin, substantially as hereinbefore described and exemplified.
8. A stabilized chlorinated, essentially straight-chain paraffin whenever obtained by a process claimed in a preceding claim.
9. A chlorinated, essentially straight-chain paraffin according to claim 5, substantially as hereinbefore described and exemplified.
10. Use according to claim 6, substantially as hereinbefore described.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19893928319 DE3928319A1 (en) | 1989-08-26 | 1989-08-26 | METHOD FOR STABILIZING CHLORINE PARAFFINS |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| IE903092A1 true IE903092A1 (en) | 1991-02-27 |
Family
ID=6387988
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| IE309290A IE903092A1 (en) | 1989-08-26 | 1990-08-24 | Process for the stabilization of chlorinated paraffins |
Country Status (6)
| Country | Link |
|---|---|
| EP (1) | EP0415250A1 (en) |
| JP (1) | JPH0390040A (en) |
| DE (1) | DE3928319A1 (en) |
| FI (1) | FI904182A0 (en) |
| IE (1) | IE903092A1 (en) |
| PT (1) | PT95104A (en) |
Family Cites Families (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE965397C (en) * | 1952-02-10 | 1957-06-06 | Hoechst Ag | Process for stabilizing chlorinated hydrocarbons against the effects of elevated temperatures |
| DE2801956B1 (en) * | 1978-01-18 | 1979-05-31 | Hoechst Ag | Process for the high temperature stabilization of polychloroalkanes and stabilizer combinations for carrying out this process |
| DE3534984C1 (en) * | 1985-10-01 | 1986-10-23 | Dynamit Nobel Ag, 5210 Troisdorf | Stabilized chlorinated paraffins and their use in carbonless papers |
-
1989
- 1989-08-26 DE DE19893928319 patent/DE3928319A1/en not_active Withdrawn
-
1990
- 1990-08-22 EP EP90116038A patent/EP0415250A1/en not_active Withdrawn
- 1990-08-23 FI FI904182A patent/FI904182A0/en not_active Application Discontinuation
- 1990-08-24 PT PT9510490A patent/PT95104A/en not_active Application Discontinuation
- 1990-08-24 IE IE309290A patent/IE903092A1/en unknown
- 1990-08-24 JP JP22140790A patent/JPH0390040A/en active Pending
Also Published As
| Publication number | Publication date |
|---|---|
| EP0415250A1 (en) | 1991-03-06 |
| JPH0390040A (en) | 1991-04-16 |
| PT95104A (en) | 1991-04-18 |
| DE3928319A1 (en) | 1991-02-28 |
| FI904182A0 (en) | 1990-08-23 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| US4622267A (en) | Microcapsules having capsule walls formed of aliphatic diisocyanate and diamine | |
| US3806463A (en) | Microcapsules for carbonless copying paper | |
| DE2163658C3 (en) | 3- <2-Alkoxy-4-aminophenyl) -3- (3-indolyl) -phthalide and pressure-sensitive copier papers that contain them | |
| EP0067793B1 (en) | Pressure or heat sensitive recording materials | |
| DE2542365A1 (en) | CHROMOGENIC UREIDOFLUORANE COMPOUNDS, THE PROCESS FOR THEIR PRODUCTION AND THEIR USE IN COPYING SYSTEMS | |
| DE2423533A1 (en) | 3-INDOLYL-3-PHENYLPHTHALID COMPOUNDS, THE PROCESS FOR THEIR PRODUCTION AND THEIR USE IN PRESSURE-SENSITIVE COPY MATERIAL | |
| US3952117A (en) | Method of desensitizing | |
| US4039207A (en) | Recording sheet | |
| DE2219556C3 (en) | Recording medium coated with a chromogenic material | |
| IE903092A1 (en) | Process for the stabilization of chlorinated paraffins | |
| EP0795590A2 (en) | Emulsion ink for stencil printing | |
| PT92861A (en) | INTERFACIAL POLYMERIZATION PROCESS FOR PRODUCTION OF AN EPOXIDE MICROCAPSULES AND PRODUCTION OF COPY SYSTEMS WITHOUT CARBON | |
| US4071469A (en) | Solvent composition for use in carbonless copy systems | |
| US4295888A (en) | Solvent compositions | |
| DE2640196C2 (en) | Dye solvent preparations for pressure sensitive copier systems | |
| US3981735A (en) | Process for making a stable, relatively high concentration, solution of an organic color-reactive colorless dye in oil | |
| CA1226438A (en) | Carbonless paper coating formulation | |
| US3979327A (en) | Dye solvents for pressure-sensitive copying systems | |
| DE69131031T2 (en) | Heat-sensitive recording material and process for its production | |
| DE2753816B2 (en) | Solvent mixture and its use in copier papers | |
| US5458974A (en) | Microencapsulated composition containing solvent including triisopropyylbiphenyl | |
| US4216112A (en) | Pressure-sensitive microcapsules containing alkylnaphthalene solvent and process for their production | |
| IE903966A1 (en) | Process for the stabilization of chlorinated paraffins | |
| DE3210191A1 (en) | METHOD FOR PRODUCING A SHEET COATED WITH ACCEPTOR | |
| DE1946681C3 (en) | Process for the production of a clay-coated paper for pressure-sensitive copier papers |