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Патент USA US2406298

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, Aug. 20, 1946.’
E. G. KING
CONTAINER CLOSURE
Filed June 50, 1944
' 2,406,298
Patented Aug. 20,1946
2,406,298
UNITED STATES‘ PATENT OFFICE j
CONTAINER CLOSURE
Ellis Gray King, Pittsburgh, Pa, assignor to Arm
strong Cork Company, Lancaster, Pa., a cor
poration of Pennsylvania.
Application June 30, 1944, Serial No. 542,894
17 Claims. (01. 215-40)‘
2
This invention relates to container closures in
cluding sealing elements and is primarily con
cerned with a container closure including a seal
ing element formed of a relatively tough, ?exible,
cured alkyd resin consisting of the reaction prod
not of a saturated aliphatic dibasic acid, propy
lene glycol, and an unsaturated aliphatic dibasic
acid. The particular acids and the proportions
thereof which may be used to achieve my new
results are more fully hereinafter set forth for 10
. only certain acids in relatively limited propor
tions may be used.
Closures are used with a large variety of con
'
,
.
many of those alkyd resins modi?ed with a drying
oil do cure to‘ a tack-free condition, the drying oil
tendsto impart, taste and odor to the contents of
the container, , especially "if there is a small
amount of oil present that has become rancid.
It is an object of this invention to provide a
new and improved closure comprising a closure
shell and» a sealing element formed of an alkyd
resin‘ and especially to provide an alkyd resin
which can be readily ?owed into a closure and rel
atively quickly cured to an insoluble, infusible,
and tack-free‘ condition at a relatively low tem
perature.
.
tainers, such as bottles, jars, cans, pails, andthe
I have discovered an improved container clo
like. A sealing element or liner is required insub 15 sure comprising a shell of any desired con?gura
stantially all types of container closures. These
tion and a sealing element of a flexible, resilient,
liners must be relatively tough, ?exible, and re
tough, and tacksfree, substantially insoluble and
silient so that a tight seal is formed between the
infusible ‘alkyd resin which is particularly ac
closure sealing element and the lip of the con
ceptable as a closure lining material. _ This alkyd
tainer and must be su?iciently devoid of cold 20 resin consists of the reaction product of from 146
?ow so that the seal is maintained inde?nitely.
to 365. grams of a saturated, aliphatic dibasic acid
The liner should be impervious to gas even at
. containing 4 to '10 carbon'atoms; one gram mo
elevated temperatures and pressures and must
lecular weight of an unsaturated, aliphatic di
not impart an objectionable taste or odor tolthe
basic acid containing 4 to 5 carbon atoms and in
, food or beverages within the container. Further, 25 which the carbonyl groups are attached to two
the sealing element should be non-tacky so that
different carbon atoms and in which the carbon
portions thereof will not adhere to the container
to carbon double bond is conjugated with at least
lip and be unsightly when the closure is removed
one of the carbonyl double bonds; and propylene
and must be relatively insoluble and infusible
glycol in an amount su?icient to condense with
so as to be substantially unaffected by a large 80 said acids and form a condensation product hav
variety of container contents.
*
.
ing an average molecularweight of at least 1,000.
Certain compositions have been proposed or
This condensed alkyd resin has the important ad
used heretofore as materials suitable for use in
vantage in that it can be readily poured intoa
‘container closures as sealing liners. For example,
closure shell and. relatively easily cured to form a
rubber and rubber compositions have‘ been used, 85 highly satisfactory sealing element. The fact
but rubber, and especially vulcanized rubber,
that the resin can be poured into the closure shell
tends to impart an objectionable odor and taste
and cured is highly desirable in that the preform
‘to the container contents. Alkyd resins which
ing and insertion problems are eliminated. For
are the reaction product of a polyhydric alcohol
example, a large stock of preformed sealing ele
and a polybasic acid have, in general, been found 40 ments need not be carried in stock and an adhe
to have serious drawbacks which.makethem un
sive need not be used for adhering the preformed
desirable as sealing elements in closures. For ex~
element within the closure shell. Further, the
ample, alkyd resins of the saturated dibasic acid
necessity for the relatively complicated and ex
polyhydric alcohol type cure by condensation,
pensive machinery normally used for inserting
yielding water which tends to produce a porous 45 preformed sealing elements is eliminated.
structure which will not form a gas-tight seal.
These and other advantages and objects will
Further, these resins require extended periods at
become more apparent when considering the fol
high'temperatures to effect curing and, what is
lowing detailed descriptionand the accompanying
most important, these resins are too viscous to
drawing, in which:
'
,
be poured readily into a closure for forming there 60 Figure 1 is a sectional view of a crown type
in a sealing element. Reducing the reaction time
closure embodying my invention;
so as to produce less viscous resins does not solve
Figure 2 is a plan View of the closure of Figure
the problem for such less viscous resins require
1; and, .
even a longer time for curing and produce even
Figure 3 is a sectional view of another closure‘
more water during‘ condensation. Many of the‘ 55 also embodying my invention.
,
other alkyd resins cannot bereadily cured. While
Referring more particularly to Figures 1 and
urated dibasic acid is relatively critical. I have
discovered that for each gram molecular weight
of unsaturated dibasic acid, I may employ from
146to 365 grams of the saturated dibasic acid. -
2, a'crown closure!) comprises a shell '6 and a
‘ sealing element 1. The sealing element 1 is shown
in the form of a disk but may be in the form of an
annular ring as shown in Figure 3. Whenthe clo
_'When the unsaturated dibasic acid ismaleic acid,
fumaric ‘acid,v or maleic anhydride, I’ prefer to em
sure 5 is placed on a container, such as a bottle,
the sealing element 1 engages a lip’ to form a seal.
ploy‘ from .2,_19[to» 292 grams of saturated dibasic
Figure 3 shows I a different type of closure 8.
acids‘ Thusj‘I may react’ from 1.0 to 2.5 mols of
comprising a shell 9 having an annular groove l0
formed therein. The groove I0 contains an an: .10 adipic acid with one mol of maleic acid, fumaric
acid, or maleic anhydride, though I prefer to re
nular sealing ring H.
r
r
.My new closures are not limited to anypartio.-_ . act ._fro,m,1.5 to 2.0 mols of adipic acid with each
mol of maleic acid, fumaric acid, or maleic anhy; '
, ular shape or design of either therclosure shell or
dride.v It has been discovered, for example, that. '
the sealing member though Ijam primarily con--v ~
if the same number of mols of succinic acid are
cerned with the well-known crown-type closure.»
used as speci?ed for adipic acid, the resultant
resinis too. hardto form a satisfactory closure
such as is shown in Figure 1.,
My new closures comprise .aisealingelement -
sealing element, but if succinic acid or any of the '
1 formed of an alkyd resin. The alkyd resin must .
be prepared from amixture comprising a satu4
rated aliphatic dibasic acid, propylene glycol, an
other ‘saturated dibasic .acids are substituted in’
an amount equal to'th‘e weight of adipic acid
4 to 10 carb'onatoms may be, for’ example, suc
used; I- prefer toemploy adipic acid as the-'satui
rated dibasic acid andeeitherrmaleic acid, fumaric
an unsaturated aliphatic dibasic acid.
, '20 spe'ci?edgvthen suitable resins are produced.
' 'whileiany-ot theaforementionedacids may be
' The saturated aliphatic dibasic acid containing’
v,cinic acid, adipic acid, sebacic acid, or the like.
acid, or maleic anhydrideas the unsaturated di
' While alkyd. resins can be prepared from other
saturated aliphatic acids and other polybasic 25
acids,» such other acids are not included within
basic
acid.‘
7‘
~
‘
.
-‘
‘r
'
'
'
If a' greater amount of the'csaturated' dibasic
acid-relative to the- amount oflunsaturated- di'-‘
basic acid vis -emp1oyed;=the alkyd resin may not
the present invention for they are unsatisfactory.
ri‘he unsaturated dibasic acid may be any un
saturated aliphatic dibasic acid containing 4 to 5
' cure, or" if itldoes, it is relatively softland tends
carbon atoms in which the carbonyl groups are 30 to crack under pressure and may-be tacky. If'a
smaller amount of saturated dibasic acid relative
attached to two di?erent carbon atoms and in
to the amount of unsaturated dibasic acid is used,
which the carbon to carbon double bond is con
the‘ resin is too hard and does, not compress su?i
jugated with at least one of the carbonyl groups.
oiently to form a satisfactory sealingelement; I
For example, maleic acid or anhydride, fumaric
acid, itaconic acid, citraconicacid, and the like,
especially prefer to- employ‘ from 1.5 vmol to 2.0V
or mixtures thereof, may be used, though wepre
fer‘irnaleicracid, maleicanhydride, and fumaric
acid. Malic acid which yields fumaricacid, ma; _
leic anhydride, and water upon being heated to
sealing element must retain relativelyrhigh car
the reaction temperature can‘ be used, for it is
Withthe above-mentioned D'roportionsiof' acids,
itris' only intended to include propylene‘rglycol as‘
the Vpolyhydric alcohol. -While~I prefér'to employ
mols of adipic acid foreach mol of maleic acid for
it has been found'thatthe resultant resi‘nis ‘espe
cially'useful for crown type closures Where-the‘
bonation pressures.
the products, fumaric acid and maleic anhydride, '
which react; Fumaric acid at the temperatures
of the reaction forms’ maleic anhydride and is,
therefore, a full equivalent of maleic acid. It is
wellrecognized that anhydridesof such dibasic
acids are the full equivalents of the acids.
be present an excess amount of the acids in the
above-mentioned ratios or there may be present]
saturated aliphatic dibasic acid, maleic acid has 5,
'
'
_
l
_
'
50
o=o'-—o,=c-o=o
.
~
l
,OH'H
l j) H
H
and contains two carbonyl groups,
'
an excess amount of the glycol so long as the ex
cess acids or glycol are not present in an amount
suf?cient to prevent the formation by condensa
tion'of a soluble, fusible resin having an average
molecular weight of at least 1,000; When there
are‘ present in the reaction mixture exactly, equal
molal amounts of glycol and acid, each condensa
tion polymer'on- the average has one terminal
hydroxyl group and one terminal carboxyl' group,
-o=0
'
‘
l the propylene glycol in a-molal amount equaljto
the total molal amount of both acids, there may’
' To further illustrate the de?nition of the un
the formula,
;
1
These carbonyl groups are connected to two dif
ferent carbon-atoms. While in maleic acid the
Whereas, if there is an excess amount of either
acid or glycol; thelpolymers» cannot condense‘
carbon, to carbon double bond is conjugated with "5 without lossof theiconstituent in excess beyond
each of the carbonyl double bonds, it is only nec 60 that point where all terminal groups are the
same, that is, Where all terminalgrou'ps are'either
essary for the carbon to carbon double bond to be
conjugated with one of the carbonyl groups, as in‘
itaconic acid where the formula is written as ‘
n .
‘
Y The sealingrelement of' relatively infusible ‘and
' '~ insoluble‘cured-alkyd resin is produced as thereev
sult- of two di?erent' types of' chemical‘reactions:
on
H_t=C_t=»o
hydroxyl groups or carboxyl- groups.
The ?rst reactionjcomprises an esteri?cationfor.
- Y
condensation reaction in which'the acids and the
alcohol combine with the-elimination of water to
form a ?uid resin of relatively'low viscosity. In,
70 the'second- reaction, there is e?ected a cross-link;
ing of the polymers “formed by- condensation
H0 0 o em -
As long as the grouping
through the double bonds ofithe unsaturated acid?
is present, the unsaturated aliphatic acid‘ comes
present in such polymers‘ to produce a relatively .
within the term .“conjugated.”
infusible and insoluble cured alkyd resin consist"
'
'
i
.
The ratio of saturated'dibasic: acid to ‘unsat
ingrof‘relatively large-complex polymers." I p‘re'» ,
2,406,298‘
5.
‘fer to curethe alkyd’ resin in an inert atmosphere,
of maleic anhydrlde, and‘3.5 mols of propylene '
‘such as carbon dioxide, nitrogen, or the‘like, with '
the'aid-of an organic peroxide catalyst,- such as
glycol.
H
v.
I
..
benzoyl peroxide,‘ though the resin may bejcuréd
‘Closures were prepared as follows‘z“ ~
to a tack-free condition in anyother satisfactory
manner.
I
'
'
i
_
‘i
1
»
'
Maleic acid _____ __,_'_ _________ __>__‘_.‘;____..' 5.294
' The benzoyl peroxide is a solid'a'nd' maybe
Adipic acid _______ __‘; __________ .._-____;’__ 876.6
added to the resin in any known manner, though
I prefer tov dissolve it in styrene and then add
Hydroquinone ______________ __~___>____V___.
10
this solution to the condensed resin to aid in our
ing'the resin. The use of styrene is advantageous
in that it increases the fluidity of the resin with
out causing bubbles in the resinv during curing.
Lhaveused up to 30 parts of styrene to 100 parts
0.2
The ingredients were mixedrand heated slowly
to 200° C. in 41/2 hours. A, conventional trap
wasv installed and 30 cc. of xylene was added and
' the heating continuedfor 2.1 hours,“ the water
formed during the reaction being removed by'
of resin, though only about 10 parts by'weiglht 15 azeotropic distillation. A vacuum of 27 mm. of
of thestyrene polymerized, the remainder being
mercury was'applied and the heating continued
evaporated during-curing. V The‘ styrene tends to
increase the toughness of the resin and, there
'\ number of v32.4 and a molecular ‘weight of about
at‘200° C. for4 hours. The resin had an acid
fore, a slightly smaller amount of'unsaturated
1730.
‘
.
~
acid may be. used. Alternatively, the benzoyl 20
peroxide may be dissolved in benzene andyadded
to the condensed resin and the benzene then
follows:
evaporated'or the benzoyl peroxide‘may be added
in‘ solid fonn on ' a carrier such as calcium
The above'resin ________________________ __'
20
Iron oxide _____________________________ __
20
Styrene - _'_ ___________________________ __'__'
0.1
0.9
sulphate.
@
Closures were prepared from this resin as
'
'
‘
,
_
.-
_,
Grams
25 Benzoyl peroxide _______________________ __
I prefer to form' the sealing element within
the closure by pouring the relatively ?uid resin
The benzoyl peroxide’ was dissolved in the
resulting fromlthe ?rst-condensation reaction
styrene and thoroughly‘mixed with the other in
into the closure seal and thencuring the alkyd
resin. If desirable, the alkyd resin ‘ingredients 30 gredients. The mixture was poured into .crown
may be esteri?ed, cured by molding in the form V shells and cured under ,COz gas. ‘These crowns
were applied to bottles containing 4.5 volumes of
dissolved CO2 gas and retained 'carbination ‘after
of sheets and then annular rings ordisks ‘may bev
die cut therefrom andsuch a preformed sealing
element inserted into the closure.
one week at 120° F.
‘ The following examples are intended to further 35
illustrate my invention without limiting it to
the exact proportions‘ or ingredients set forth ,
except as de?ned by the appended claims.
'
‘
" Example 1
r
_
acid
Propylene
‘
'
‘
___'
,
‘
-
>
either the form of disks or annular rings can be
40 shells to produce highly satisfactory closures.
Example 3
’
A condensed alkyd resin was preparedasdeQ
Grams
Maleic anhydride_‘_; __________________ __
Adipic
"
cut from the sheet andthen placed within closure
'
. Closures were prepared as follows:
‘
"
Alike ‘mixture was readily cured under CO2
gas in the form of a sheet 1/8" thick and another
cured in a closed mold. Sealing elements in
_;_
v49.0
scribed in ‘Example 2 and then compounded as
182.6
glycol‘. ______________ _a _____ __ ‘133A
45
follows:
“
‘
I ‘_
_Parts
-These ingredients ' werernixed and heated ' Resin
_________ _'_ ____________________ __
100
gradually‘ to 200° C. in one hour and the water
Red slate power _________ _.'_ _____ _'_ _____ __
66.7 '
evolved was removed bya condenser. A conven
Benzoyl ‘peroxide _____________ _‘_..____'____‘ 0.5
tional trap was then installed, 25 cc. of xylene 50 Styrene ; _____ __' ______________________ __ ‘4.5
was added, and the heatinglcontinued for 11/2
hours,'_th__e7water formed‘ during the condensae
tion being removed by azeotropic distillation. ' The
Thisomixture waspoured, into a. crown closure
and-cured under CO2 gas. ‘I'hecrowns retained
carbonation even at pasteurization temperatures,
trap was then removed and a vacuum of'ab'out
12 mm. of mercury applied and the heating con 55 of 150?’,F. followed by storage for one‘week at~120°
F.- These crowns were tested on containers con-.
tinued at about 200° C‘. for 2 hours and 50 min
taining 4.5 volumes of dissolved CO2 gas.
utes. During the entire process, a small stream
of‘nitrogen was passed through the apparatus so ~
‘Example 4
that the resin was condensed under an inert at
mosphere. The acid number of thecooled resin
was 37.8 and its molecular Weight'was about 1500.
Example
_ An alkyd
2 and
resinthen,’
wascompounded
prepared as as
described
follows;v
' This resin was compounded as follows:
.
The‘above resin", ______________ "grams" 25
Red slate ________________________ ~_doe__,_ 16.7
Styrene including 10% of benzoyl 'perox-
“ 65
ide s ______________________ __‘_____'_'_cc__ v1.4.6
' IThese-materials were mixed and molded at 257‘?
F. for 40‘minutes. The resultant sheet wasnon
tacky. and . resilient.
Annular rings were V out 70
fromthis sheet and placed'within closure ‘shells .
to form therein a satisfactory sealing element.
These rings were softer than preferred. ‘ »
p
_
Parts
Resin ___________ _‘___'__" _______________ __
50
Filler
5O
______ _,_';=_...‘___‘__'__"_..;_.__'.;_i_'
Benzene
' , ____ .__
_____ __'_ ________________ _a_____
1“
Benzoyl peroxide ____________________ __-__
0.25
' Fcurldi?erent'rnixtures were ‘compounded in
the above proportions using di?ierent'?llers. The
?llers were calcium carbonate, “Gartex” vwhich
is ?nely divided 85% silica and 15% glassQpotter’s
?int, and iron oxide. ., All of‘these compositions
after being poured into closure shellsand cured
> ‘In this example, the amount of the ingredients
retained carbonation of from 4 t0'4.6 volumes
' areequivalent to 2.5 molsofvadipic acid, one mol 75 after'onewe'ek at.120°~F. sli- '
"
~11
2,406.3 9.8.
7
,
‘
.
Examnle?
I
._
..
,'
I
11-‘;
2.00“ C... carbon-dioxide vheme passed-through the
.
Closures were prepared; as follows;
.
r
'
'
v
'
~'
" f
1
.
apparatus. 7 After a further 45 ‘minutes, , a.._trap
containing calciumv chloride and calcium carbide
Partsv
Maleic anhydride ___;_'_j_‘_._~ _______ __v_,,__'_y__v_v;_rv 768.6
, Adipic acid ____ ______________ _'___;___
Propyleneglyr'ol
7'
'
_
hwas'gattached, and .suliicient xylene added tothe,
1_ 102.3'
‘
.8 ,
' ever a period-oi ‘one. hour to aitemperatureaoi 1
reaction mixture so that there would be .a-con-H .
tinuous. re?ux‘ through’, the trap; After, 7,5 ‘hours
~and.2_5 minutes atiabout 200° 0-, thetrap was
removed and carbnn dioxide was blow-11 through
109.;5
Hydroquinone n;wahuv?mgdnuQ_;_;__. , 0.2
" .‘The ‘ingredients-were‘ mixed’ and ‘heated grad‘-v
ually‘ to (200‘? 1C. and then heated for . an additional
the resin for 30 minutes to remove the xylene.
The acid vnumber was 22.1‘ and the molecular
period -of'.3.5 minutes, the Water evolved ‘being. re
moved 'byazeotropic: distillation. The resinous
weightlwas about'2500;v
"
"
'
e
'
-
resin was mixed and curedas in?ows: >
mixture. .was‘then» heated under vacuumifor 4
hours and 25 minutes-at 200° v,to;,220°aC_. ‘The
resin. had. an acid .numberof134l2 and‘ a, molec
ular-weight'of about 1.640;
-
f
'
'
'
Satisfactory sealing elements ‘can: be readily
formed from this; resin ~or:from mixturesof this
resin and ?ller by any of the methods previously
described in the examples. I.
.
p
_
'
'
12.0
’
i
This mixture was poured into crown shells and '
cured‘in an atmosphere of carbondioxide for 35
Example 76 >
minutes :at-l2759' C. The crown closures“. were .ap
.An alkyd resin was prepared as follows: .
I
.
.
Fumaric acid
.
plied‘ to bottles; containingyl.5j_ volumes. of v-dise
solved CO2 gas and carbonation was retained ‘for’
Parts
‘
_
_
Adipic.acid-.------.--.-._
'
___
‘69.17.
one weekat 120° F.
.---.-.-_.-.-..-.--,.-.--- 175.:3
Propylene glyc0l__v______1_> _______________ __
r
140
heating gcontinued, the ‘water evolved being're
moved -.-by azeotropic distillation.
'7
‘
V
.
Example 9?
»
7
An alkyd resin may. bé prepared from the-fol;
’ ‘The ingredients were mixed (and heated to:200°
C. in,.,3.0 minutes.:_ Xylene was added. and the
'
lowing ingredientszrl
so
Vacuum was
Sebaoic
acid
f
V
v
.
.
"
v
.
--
'
,
‘
.
H
‘
v
Maleic anhydride__~__,-__,_ _,_vl__,___j___'_r__
applied and ‘the heating continued until 6 hours
.
'
.
Proplene glycol (slight excess) ; _____ _'__
The resin had an acid number .of
35.4.. This resin may be used to‘ form highly 35 These constituents were reacted as ‘described
satisfactory sealing elements either by itself or
under "Example '9 except that after‘ .3 hours'and '
when compounded as previously described.
‘
57 minutes, the acid number _was41.3.and-after <5
hours .was 23.9. Thistheavyresin may be com
7
Example]
pounded and used in closures as described in any
had elapsed.
Closures were prepared as follows:
I
of vthe preceding examples.
Y
'
Maleic anhydride _____ _gl_r______r_ _______ __ 137.2 ‘
The particular alkyd ‘resins whichv I3 have Joe; ‘
scribed may be used with or without ?llers, though.
Succinic acid__v ____ _;
I preferv to. employ. ?11ers as they reduce the. test
,
.
'
,
Parts
p _____ _'__,___v___ 330.4
. Propylene glycol_'___;___
of the‘ sealing elements. Any iiilecsuch aster
example. calcium -cwbonate.-. slate. iron oxide;
:___'___'_.___._' ____ __ 329.2
The ingredients were mixed and heated to 200°
tripoli, potter’s ?int, and the like or mixtures
thereof, may be-usedlin widely varying ‘propor
‘C‘.,for 21/2 hours. Xylene was added and the heat- 7‘
mg i continued until 6.6 vhours had elapsed, the
water evolved being removed by azeotropic dis
ti'ons.
1
,
>
‘
‘
~
'
_
1
'
Having (described my invention indetail, "it is
tillationJ‘Th‘e' resin‘had' an acid numberfof 40.4 5.0. obvious'that some features may be: 1 employed
and a molecular weight‘? of about 1400. "
‘
without others. all without departing from :the '
sprit or scopeof my invention‘d'e?ned in’th‘e ac
This'resjin was compounded as follows: .. :
v.
V
_
‘
1-"'-"~P_arts"
companying
The‘ab’o've resin ______ __‘:__~___' ____ __“____'____ 100
Styrene __"_ ______________ __¥__' ____ __~_'_';____
4.5
B'enzoyl-peroxide __________________ __>_'__¥__' 05
ijI'claim:
claims:
'
-
'
'..
.,
'
~
J
‘
"
-
'
'
r
' l. A closure comprising a shell and a sealing
55
element including a cured alkyd resin consisting
of 1the cured condensation reaction-product of "
The ‘benaoyl peroxide was dissolved 'in the
styrene and the ingredients mixed and then
poured into a crown type closure and cured. "A '
r from 146 to 365 grams of asaturatedgaliphatic
dibasic acid containing 4 to‘ 10 ‘carbonvato'msi '
one gram molecular weight of an‘ unsaturated,-v
tougha?lm which held carbonation during pas
aliphatic dibasic acid containing from .~4j¥to">5
teurization ‘and storage was formed. '
\
'
carbon atoms and in which the two carbonyl
groups are connected to’ two different carbon
Example 8
atoms and in which the carbon to carbon double
Closures-Were prepared‘as'follows:
.
j A
6.5, bond'isconjugated with at least one of the car
bonyl double bonds; and propylene glycol in an
amount su?icient to condense with said acids‘ and
form-:a resinous condensation productfhavingi-an
Adipic .acid ____ __-_ __________ __'~_Y_'__"_______' 116.8
Itaconic acid _________ ___ _______________ __
52.1
Propylene} glyco1_"__’___‘_ ________________ _;
Propy1ene“g1ycol‘(1% excess) ______ _..'___'__
91.3'
>0;9
"In this example, there are tWo .mols of adipic
acidv for one mol of itaconic acid.
_
* .
‘
The reactants were placed in a 3-neck ‘?ask
?tted “with astirrer, thermometenand iWidmer
V average'molecular .weightof -..at.l_east'1‘,00§0:
70
I.
.2. A" closuref comprising a'ljshellxand-.aj:sealing
element including; at- curedialkyd resin- consisting ‘
of. the cured condensation reaction‘. product of r
from 219 l to 292; gramspf. a saturated, ‘. aliphatic
‘ dibasic .acid- containing .4 -:to- 10 .carbonéatoms;
column. The temperature ~:was :raised gradually 75 one. gram molecular? weight; Ora materiali selected
2,406,298
10
from the group consisting of'rnaleic acid, fumaric
acid, andrmaleic anhydride; and propylene glycol
from 1.5 to 2 mols of adipic acid;_'l'one mol of an
in an amount sufficient to condense with‘ said
acids and 'form a resinous condensation product
from 4‘to 5 carbon atoms and in‘which the two
lliaving an average molecular weight of at least
carbon atoms and in which the single carbon to
carbon double bond is conjugated with at least
one of the carbonyl double bonds; and propylene
,000.
.
.'
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.,
.
unsaturated, aliphatic dibasic acid containing
carbonyl groups are connectedgto two di?erent.
3. A closure comprising a shell'and a sealing
element including a cured alkyd resin consisting
glycol in a molal amount'substantially equal'to
of the cured condensation reaction product of
the total molal amount of both said adipic acid
from 146 to 365 grams of a saturated,v aliphatic 10 and said unsaturated acid.
1
' ‘
dibasic acid containing 4 to 10 carbon atoms;
9. A closure comprising a‘ shell and a sealing
one gram molecular weight of an unsaturated;
element including a cured‘ alkyd resin consisting ,
aliphatic dibasic acid containing from 4 to 5
of the cured condensation reaction product of
carbon atoms and in which the two carbonyl
from 1.0 to 2.5 mols of adipic‘ acid; one‘gram
groups are connected to ‘two different carbon 15 molecular Weight of a material selected from the
atoms and in which the carbon to carbon double
group consisting of maleic acid, fumaric acid,
- bond is conjugated with at least one of the car
and maleic anhydride; and propylene glycol in
bonyl double bonds; and propylene glycol in a
an amount su?icient to condense with said acids
molal amount substantially equal to thetotal
and form a resinous condensation product hav
amount of both said saturated and said unsat 20 ing an average molecular weight of at least 1,000.
urated acids.
10. A closure comprising a shell and a sealing
4. A closure comprising a shell and a sealing
element including a cured alkyd resin consist
element including a cured alkyd resin consisting
ing'of the cured. condensation vreaction product
of the cured condensation reaction product of
of from 1.5 to 2.0 mols of adipic acid contain
from 219 to 292 grams of a saturated, aliphatic 25 ing one gram molecular weight of a material
dibasic acid containing 4 to 10 carbon atoms;
selected from the group consisting of maleic acid,
one gram molecular weight of unsaturated acid
fumaric acid, and maleic anhydride; and propyl
selected from the group consisting of maleic acid,
ene glycol in an amount sufficient to condense‘
fumaric acid, and maleic anhydride; and propyl
with said acids and form a resinous condensa
ene glycol in a molal amount substantially equal 30 tion product having an average molecular weight
to the molal amount of both said saturated and
of at least 1,000.
_
said unsaturated acids.
11. A closure comprising ‘a shell and a sealing
5. A closure comprising a shell and a sealing
element including a cured alkyd‘ resin consisting
' element including a cured alkyd resin consisting
of the cured condensation reaction product of
of the cured condensation reaction product of 35 from 1.0 to 2.5 mols of adipic acid; one gram
from 1.0 to 2.5 mols of adipic acid; one mol of an
molecular weight of an unsaturated acid se
unsaturated, aliphatic dibasic acid containing‘
1ected from the group consisting of maleic acid,
from 4 to 5 carbon atoms and in which the two
fumaric acid, and maleic anhydride; and propyl
carbonyl groups are connected to two diiTerent
ene glycol in a molal amount substantially equal
carbon atoms and in which the‘ carbon to carbon 40 to the total molal amount of both said adipic
double bond is conjugated with at least one of the
acid and said unsaturated acid.
carbonyl double bondsyand propylene glycol in an
12. A closure comprising a, shell and a seal
amount suf?cient to condense with said acids
ing element including a cured alkyd resin con- '
and form a resinous condensation product hav
sisting of the cured condensation reaction prod-t ‘
ing an average molecular weight of at least 1,000.
uct of from 1.5 to 2.0 mols of adipic acid; one
6. A closure comprising a shell and a sealing
gram molecular weight of an unsaturated acid
element including a cured’ alkyd resin consisting
selected from the group consisting of maleic acid,
of the cured condensation reaction product of
fumaric acid, and maleic anhydride; and propyl
from 1.5 to 2.0 mols of adipic acid; one mol of an
ene glycol in a molal amount substantially equal
unsaturated, aliphatic dibasic acid containing 50 to the total molal amount of both said adipic
from 4 to 5 carbon atoms and in which the two
acid and said unsaturated acid.
carbonyl groups are connected to two different
.13. A closure comprising a shell and a sealing
carbon atoms and in which the single carbon to
element including a cured alkyd resin consisting
carbon double bond is conjugated with at least
of the cured condensation reaction product of
one of the carbonyl double bonds; and propylene
from 1.0 to 2.5 mols of adipic acid; one mol of '
glycol in an amount sufficient to condense with
maleic acid; and propylene glycol in an amount
said acids and form a resinous condensation
sumcient to condense with said acids and form
product having-an average molecular weight of
a resinous condensation product having an aver
at least 1,000.
'
'
age molecular weight of at least 1,000.
’
7. A closure comprising a shell and a sealing 60
14. A closure comprising a shell and a sealing
element including a cured alkyd resin consisting
element including a cured alkyd resin consist-‘ ‘
' of the cured condensation reaction product of
ing of the cured‘ condensation reaction product
from 1.0 to 2.5 mols of adipic acid; one mol of
of from 1.5 to 2 mols of adipic acid; one mol of
an unsaturated, aliphatic dibasic acid contain
maleic acid; and propylene glycol in an amount
ing from 4 to 5 carbon atoms and in which the 65 su?icient to condense with said acids and form '
two carbonyl groups are connected to two differ
a resinous condensation product having an aver
ent carbon atoms and in which the single carbon‘!
age molecular weight of at least 1,000.
to carbon double bond is conjugated with at least
15. A closure comprising a shell and a sealing
one of the carbonyl double bonds; and propylene
element
including a cured alkyd resin consisting
glycol in a molal amount substantially equal to 70
of
the
curedcondensation
reaction product of'
the total molal amount of both said adipic acid
about 330 parts by weight of succinic acid; about
and said unsaturated acid.
‘
137 parts of maleic anhydride; and propylene
8. A closure comprising a shell and a sealing
glycol in a molal amount substantially equal to
element including a cured alkyd resin consisting
the total molal amount of both said succinic acid
of the cured condensation reaction product of 75 and said maleic anhydride.
'
11
'
‘
<16; Auclosure comprising 1a shell and a sealing
grams of‘ a saturatedaliphaticJdibasiclacidxcon
element including a cured alkyd ‘ resin consisting
taming 4M0 .10-carbon- atoms ; l one-gram molecular
of ithe‘rcur'ed condensation reaction product vof
weight ‘of an unsaturated, aliphatic dibasic acid
about 1-16,_parts" by Weight of .aclipic acid; about
{containing ftom~4 to‘5 carbon atomsand in which
52 parts by weight ‘of itaconicjacid; and propylé 5 the two carbonyl groups are connected with two
eneiglycol in a molal amount substantially equal
~ different carbon atoms and in which the single
to the total mol'al amount of both said adipic @ carbon to carbon double bond is conjugated with
acid-and said ita'conic acid.
'
V
at=1east vone<of the 'carbonylldouble bonds; and
‘ "117
:closure comprising va shell andva sealing
propylene glycol in amolal amount substantially
element including a binder’ consisting of at least :10 equal to the total molal amount of both said sat
90%"b_y_-weight ‘of a1 cured alkyd resin and not
u-rated dibasic acid (and said unsaturated dibasi'c
more than 10% by'weight of polystyrene, said
V
icuredr'iaikyd
resimconsisting ‘of the cured con
densation reaction product ‘of from 1146 to 365
acid.
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ELLIS "GRAY KING;
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