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Патент USA US2115797

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Yatenteil May 3, 1938
l‘
g
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’
UNITE-D STATES-{PATENT oFFici: ,
WATERPROOF COMPOUND
Maurice
SocIete-Nobel
Henri Belloc,
Francoise,
Paris,
Paris,
France,
France,-a
assignor
joint
stock company
'
-
No Drawing. Application March 2. ‘1936, Serial
No. 66,697. In France March ‘I, 1935
'4 Claims. (oi. 134-13)
The present invention has for its object the, dicated remains within the scope of the inven
preparation of a waterproofcompound consisting tion by whatever process they are prepared.
oi polymerized vinyl derivatives having the Such products have the general formula:
'
chemical composition of acetals.
-
0'_CH=CH, ‘
It is well known to'waterproof paper, fabrics,
‘
regenerated cellulose and similar products by
[R—(’II
means of varied solutions containing in general
waxes or para?in- said compounds are consii-
I
_
0~on=cn
in which R is an aliphatic radical which can be
tuted generally by nitrocellulose, a wax or parailln H or CH: according to ‘whether the product is
10 and a suitable solvent mixture which can also ‘prepared by means of formaldehyde or acetalde- 10
contain 'an oil. iF'inally. compounds may be used
containing acetate or other vcellulose esters or
hyde; n is the degree of polymerization of the
condensation product; it can vary‘ within wide
ethers.-
limits.
Generally. waterproo?ng coatings of this kind
15 contain a cellulose ester or ether associated with
‘
-
win therefore comprise}
a wax, a para?‘in or an oil. Said coatings have
_ a number of drawbacks.
1- They are not very adherent. particularly to
'
-
' ‘
. '
15
l. One or a plurality of condensation products.
of polyvinyl alcohol with formaldehyde, .acetalde
hyde or a mixture of the two. Said products
highly polished'supports such as regenerated cel-
serve as a, Support‘ _-
20 1111056; in Particular they are easily un?tilck by
'
2. One or a plurality of known waterproo?ng 2“
immersion in water. < _
products such as paramns, natural or synthetic
2- They are insu?iciently ?exible. thisdrewback being particularly important for water-
25
'
A suitable coating for the purpose proposed
waxes, chlorinated naphthalenes and the like.‘
.
3. One or a plurality of plasti'?ers for the
proo?ng fabrics.
_condensation product; ‘preferably insoluble in
3. The coatings‘ which contain nitrocellulose
are veryin??mmable and, Owing to this fact,
waten Compounds which are suitable for the
intended object are: alkyltoluolsulfonamides,
their application is rather delicate-
’
. - triphenylphosphate, butyl and cyclohexyl stear
4. It is rather dimcult, particularly if' nitro- ates, and the like. This list is in no way limita
cellulose 01‘ cellulose acetate 15 used as a suppm't ' tive, its object is merely to indicate nominally
30 for the' waterproo?ng bodies, to ?nd-a compound some of the products which can be used_
30
of solvents which dissolve suillciently well, on the
one hand cellulose ester, on the other hand parai-
’ 4. A Suitable solvent mixture which comprises.
in principle’ one or a plurality 61, solvents of the
this!‘ mggiztsl?sttat'gcesrgegzeifglélrftggdéonslsts
vinyl 1 condensation
product, one orroduct
a plurality
eat
i the water- rooi'i
and of
e 0
i
35 in the preparation , of compounds for
water
proo?ng papers’ fabrics, regenerated cellulose
of so v
's o
p
a “8 p
=
.
3,,
the plastiiying product. Amonst the solvents
and the like, avoiding to a great extent these 222221;‘: bzhl‘g?ge theé?logxrge‘ mglmlggli
cellulose
drawbacks
ester
by or
using
ether,
as aasynthetic
support, product
instead havof a
40 ingv the chemical composition of a polymerized
8th“noI i benm m’ toiluene
acetates’ and the like- It
ethyl
t
iand
m to
methY.
_
110 D085! 8
elill- 40
vinyl meta], These products gab he;
merate all the well lrnown solvents which can
Polyvinyl iormals or'acetals such as those ‘be 11§¢d..lihe$¢ being (very Varied Owing to the
.obtained by reacting aldehydes with more or less
saponi?ed. 'vinyi esters.
45
"
- '
-
Mixed products such as those obtained by con- i of viiry varied solvents according to their con- 45
densing polymerized vinyl esters with two alde-
hyde's; particularly‘ formaldehyde and acetic
paraldehyde. ‘
'
fact in particular that the condensation Prod
nets of polyvinyl alcohol and, of aldehyde allow
‘
‘
It is, of course, understood that the use of
.50 products having the chemical constitution ln‘-_
.stitu on.
a
_
v
_
If necessary, the compound can also contain
natural or arti?cial oils or resins, adapted to give .
it particular properties.
1 The followlne examples ii: the conditions of lo _
2,115,797
application of the invention, without limiting ‘it
in .any way:
'
-
e
kgs. of acetic paraldehyde.
polyvinylabetate, 2 litres of water, 1 litre 'of
alcohol and 5 litres of strong hydrochloric acid,
stirring and cooling'and, after a few minutes,
3 adding 5 kgs. of acetic paraldehyde, then standing
10 hours. at'room temperature.
paraflln
‘
'
>
Y parts by-weight.
Butyl
v
’
'
'
_
o
Polychloronaphthalene wax ______________ ....
5
-_ Methylene chloride _____________________ __ 700
I
~
200
‘
v
100
‘This compound should be applied hot to avoid
any precipitation of the wax.
I claim:
50
.._
.
stearate
_ _Methanol
' -
_
I >
Above described condensation product“ 100
Benzine
_
The following mixture is prepared?
1 Above ‘described condensation product 800
parts by weight.
.
The following mixture is prepared: _
densation product of vinyl acetate and acetic;
paraldehyde, obtained by adding to 5 kilos, of
Hard
_
substituting 3 kilos. of trioxymethylene for the
‘
‘ Example 1.—As a starting material, the con
15
_
’
‘ 1. A resinous liquid coating composition for
Solvent‘ _________________________ __~_____ 8000
waterproo?ng paper, fabrics and regenerated
Ethylparatoluenesulfamide _' _____ ___ _____ ___ 150
cellulose comprising a resin selected from the
The solvent will be constituted in this case as group consisting of water insoluble condensation
follows:
products of'polyvinyl alcohol and acetic paralde
'
20
'
‘.
'
5
hyde, polyvinyl alcohol and a mixture of form-' 20
aldehyde and acetic pal-aldehyde, and polyvinyl
8
2" alcohol and trioxymethylene; a minor pronol'tivn
_ of a waterproo?ng'agent selected from the group
Volumes
'Toluene ____‘______- ______________________ __
Ethyl acetate
‘
'
_
____
This compound can be applied by any means to' consisting of para?in, natural waxes, synthetic
25 paper, regenerated cellulose, fabrics, which it is
, desired to
'
water.
waxes, and chlorinated na'phthalenes, said water- '
render substantially impervious to ; proo?ng agent being present in the
a proportion {of
-' *1 1 part waterproo?ng agent to 16 to'20 parts of
.
_
Y
.i
It is advantageous to heat said compound be
.
said resin, said amount being sufiicient to in
fore use to a suitable temperature so that it's-hall - crease the water resistance of the coating; and a I
30 be completely homogeneous.
P ,.
.
Example 2.—As a starting material, a con
densation product prepared from a polymerized
polyvinylic-acetate such that at 20°, a 10% solu
tion of this' compound in ethyl acetate ?ows in
35 >300 seconds through _a hole, through which the
same volume of ‘water at the same temperature .
?ows in 15 seconds, by adding to v20 kilos. of this
polyvlnylicacetate, 9.6 kilos. of formaldehyde at
40% by volume, 2:55 kgs. of acetic paraldehyde, 4
volatile organic solvent for both the said water
proo?ng agent and the said resin in amount
su?icient to dissolve the same.
'
_
v
- 2. A resinous liquid coating composition for
waterproofing paper, fabrics and reg'eneratedcel
lulose'comprising para?in‘50 parts by weight, 800
parts by weight 91' the water-insoluble product
made by hydrolysis of 5 kilos, of polyvinyl acetate
and subsequent condensation with 5 kilos. of
acetic paraldehyde, 150 parts by weight of 'ethy'l- .
40 kgs. of. denatured alcohol and 40 kilos. of hydoJ - paratoluenesulfamide, and 8000 parts by weight
40
,chloric acid at-22° Baumé, stirring until solution of a- mixture of toluene and ethyl acetate.
is completed, allowing to remain in contact for 20 ‘ 3. A resinous liquid coating composition for‘.
hours at room temperature preferably by stirring.’ waterproo?ng paper,- ‘fabrics and regenerated
The following mixture is prepared:
cellulose comprising parailin 30- parts by'weight,
Above ‘described_ condensation product 600 _ 600 parts by weight of the water-insoluble product
parts by weight.
‘
‘
.
_,
'
_ .Triphenylphosphate- ____________ __, ____ _’__
>
100
Ethylparatoluenesulfamide _____________ __l. - 100
Hard para?ln
50
_
~
"
-'
~
Methanol ____________________ _'_ _______ __
Benzine
_________________ __-_ ____ -r ____ __'
40% formaldehyde and 2.55 kilos. of acetic par
_al_dehyde, 100 parts by weight of triphenyl
600 "phosphate, 100 partsby weight of ethylpara-v to
2160 ' ‘ toluenesulfamide, 600 parts by weight of metha-,
no], and 2160 parts by w'eight'of benzine.
treatment of fabri'cs.~ For this use and according
55 to the ‘waterproo?ng desired, it can, of course, be
of methanol and of
benzine in the proportions indicated. The applis
- cation ‘of the solution, preferably hot, will be
effected by means of a padding machine. After
_ drying, it is often advantageous‘ to calender in
.
45
30
This compound is particularly applicable to the
diluted with .the
of simultaneous hydrolysis and condensation of
20 kilos. of polyvinyl acetate with 9.6 kilos. of
4. A resinous liquid coatingco'mposition for > _
waterproofing paper, fabrics and
‘cellulose comprising 9 parts by weight of butyl
stearate, 5 parts by weight of polychlotnaphthr‘
lene wax, 100 partsEby weight of the water-_
insoluble product of hydrolysis of' 5 kilos. of poly
vinyl acetate and subsequent condensation with
.3 kilos. of trioxymethylene, -700 parts by weight
order ‘to givethe waterproofe'd fabric~ amore of methylene- chloride, 200 parts by weightof
agreeable aspect.
.
'
and 100 parts .by eight of methanol.
Emmple'_3.'—As astarting material a conden ‘ benaine,
MAURI
HENRI BEILOC. sation'produ‘ctv prepared as "in Example “1, by
53
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