Us 5154760

8/17/2019 Us 5154760

1/6

United S t a t e s Patent [ 9 ]

l l l l l l l l l l l l l l l l l I l l l l l l l l l I l l l l l l l l l l l l l l l l l l l l l l l l I l l l l l l l l l l l l l l l l l l l l l l

USOOS 54760A

P a t e n t

Number:

1 1 ] 5 , 1 5 4 , 7 6 0

M i l l e r , J r . [ 4 5 ]

D a t e

o f P a t e n t :

O c t .

1 3 , 1 9 9 2

[ 5 4 ]

POLYAMIDE RESIN COMPOSITIONS FOR

USE A S LAMINATING INK RESIN BINDERS FOREIGN PATENT

DOCUMENTS

[ 7 5 ] I n v e n t o r : George E . M i l l e r , J r ” Savannah, Ga_ 1 7 1 8 5 0 4 2 / 1 9 8 6 E u r o p e a n P a t . O f f . . . . . . . . . . 5 2 8 / 3 3 9 3

. .

C

. Primary Examiner-Mark L.

Bell

[ 7 3 ] A s s l g n e e a n y , “

p

C o r p o r a t i o n ’ W a y n e ’ A s s i s t a n t E x a m i n e r — H e l e n e K l e m a n s k i

‘ A t t o r n e y , Agent, or Firm-—William K,

Wissing

[ 2 1 ]

A p p ] . N o . : 6 1 8 , 7 6 7

[ 5 7 ]

A B S T R A C T

[ 2 2 ] F l l e d :

Nov‘

2 7 ’ 1 9 9 0 A olyamide r e s i n c o m p o s i t i o n

f o r u s e

a s l a m i n a t i n g i n k

[ 5 1 ] I n t . C l . 5 . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .

. . C09D

11/02 r e s i n

b i n d e r

i s

provided by t h e

condensation

r e a c t i o n

[ 5 2 ]

US.

C l . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 1 0 6 / 2 0 ; 1 0 6 / 2 7 ; p r o d u c t o f

d i m e r i z e d

f a t t y a c i d s h a v i n g

3 6

c a r b o n

_

5 2 8 / 3 3 8 ;

528/339‘3 atoms, a t l e a s t one d i b a s i c a c i d , a t l e a s t one C1-C4 a l k y l

Fleld of Search . . . . . . . . . . . . . . . . . . . . . . . . . . .

d i a m i n e and

a t l e a s t

one

p i p e r a z i n e _ l i k e d i a m i n e _

The

528 /3 9 3 , 3 3 8

e q u i v a l e n t s o f

a m i n e g r o u p s

i n t h e

c o m p o s i t i o n a r e

[ 5 6 ] R e f e r e n c e s

C i t e d s u b s t a n t i a l l y e q u a l t o

t h e e q u i v a l e n t s o f c a r b o x y l

U . S . PATENT DOCUMENTS

2.149.286 l/l 9 3 7 Graves

. . . . . . . . . . . . . . . . . . . . . . . . . . .

. 528/3393

4 , 0 6 6 , 5 8 5 l/1978

Sc h e p p

e t a ] . 106/27

4 , 2 4 3 , 7 0 2

l/198]

Walsh

. . . . . . . . . . .

. 1 0 6 / 2 7

4,514,540 4/1985

Peck . . . . . . . . . . . . . . ..

106/20

4,921,932

5/1 990

Tamura t a l . . 5 2 8 / 3 3 9 3

025,043

6/199] Smith . . . . . . . . . . . . . . . ..

524/607

5,026,755

6/1991 Kyeglis e t

a l .

. . . . . . . . . . . . . . . . . . . . . .

. 1 06/ 2 0

g r o u p s , where 3 0

t o

5 0

e q u i v a l e n t

p e r e c e n t o f t h e

c a r

b o x y l

g r o u p s

a r e

c o n t r i b u t e d

by

t h e

d i b a s i c

a c i d

c o m

p o n e n t

and

7 3 t o 9 3 e q u i v a l e n t p e r c e n t o f t h e

amine

g r o u p s

a r e

c o n t r i b u t e d b y

t h e

p i p e r a z i n e - l i k e d i a m i n e

c o m p o n e n t . P r i n t i n g i n k s w i t h

t h e

p o l y a m i d e r e s i n

c o m p o s i t i o n o f t h i s i n v e n t i o n a r e a l s o

p r o v i d e d .

1 5 C l a i m s , N0 D r a w i n g s

8/17/2019 Us 5154760

2/6

5 , 1 5 4 , 7 6 0

1

POLYAMIDE RESIN COMPOSITIONS FOR USE

A S LAMINATING INK RESIN

BINDERS

FIELD

OF THE

INVENTION

T h i s i n v e n t i o n r e l a t e s t o p o l y a m i d e r e s i n c o m p o s i

t i o n s

f o r

u s e

a s

l a m i n a t i n g i n k r e s i n b i n d e r s . More p a r

t i c u l a r l y ,

t h e

i n v e n t i o n

r e l a t e s t o

h i g h

p i p e r a z i n e - l i k e

d i a m i n e / h i g h

d i b a s i c

a c i d

p o l y a m i d e r e s i n c o m p o s i

t i o n s t h a t p o s s e s s d e s i r a b l e p r o p e r t i e s

s u c h a s

good

e t h a n o l s o l u b i l i t y

a n d

r e d u c i b i l i t y ,

a n d h a v e

g o o d v i s

c o s i t y s t a b i l i t y i n

s o l u t i o n .

BACKGROUND

OF

THE INVENTION

I n t h e

m a n u f a c t u r e

o f p r i n t i n g i n k s , e f f o r t s a r e c o n t i n

u o u s l y made t o

d e v e l o p

new a n d i m p r o v e d p o l y a m i d e

c o m p o s i t i o n s

u s e f u l a s p i g m e n t b i n d e r s

i n

i n k s f o r p r i n t

i n g a v a r i e t y o f

s u b s t r a t e s .

I n p a r t i c u l a r dem and a r e

t h o s e i n k s which

can b e

p r i n t e d o r l a m i n a t e d on poly

olefm

s u b s t r a t e s such a s

p o l y e t h y l e n e .

These

i n k s

must

p o s s e s s

a

number o f

q u a l i t i e s t o b e c o m m e r c i a l l y u s e f u l ,

i n c l u d i n g

g o o d

e t h a n o l

s o l u b i l i t y

a n d


a n d

g o o d

v i s c o s i t y s t a b i l i t y

i n

s o l u t i o n among o t h e r s .

P o l y a m i d e s c o m p r i s i n g

d i m e r i z e d f a t t y

a c i d s a r e

known t o b e u s e f u l i n t h e m a n u f a c t u r e

o f

p r i n t i n g

i n k s

a n d

i n

a d h e s i v e a p p l i c a t i o n s . A c c o r d i n g

t o US.

P a t .

N o . 3 , 3 7 7 , 3 0 3 ,

p o l y a m i d e c o m p o s i t i o n s i n c l u d i n g a p i

p e r a z i n e o r

d i p i p e r d y l

t y p e d i a m i n e component

a r e

d i s c l o s e d a s s u i t a bl e f o r h o t

m e l t

b i n d i n g . G o o d adhe

s i o n t o v i n y l s u b s t r a t e s

b y t h e s e

p o l y a m i d e

c o m p o s i ‘

t i o n s a r e shown, however s u c h a d h e s i v e c o m p o s i t i o n s

a r e

g e n e r a l l y p o o r l y

s o l u b l e i n

a l c o h o l

and p o s s e s s

o t h e r

p r o p e r t i e s

s u i t a b l e

f o r a d h e s i o n

b u t

g e n e r a l l y

u n s u i t e d

f o r

a p p l i c a t i o n s

a s

a n i n k

r e s i n

b i n d e r .

U . S . P a t . N o . 3 , 6 5 2 , 4 6 9

t e a c h e s

p o l y m e r i c f a t t y a c i d

p o l y a m i d e r e s i n s o b t a i n e d b y

r e a c t i n g

a n

a c i d

m i x t u r e

o f

a

p o l y m e r i c

f a t t y

a c i d

and a low a l i p h a t i c m o no c ar

b o x y l i c

a c i d w i t h a n amine

m i x t u r e

o f

a n a l k y l e n e d i

a m i n e a n d

a p o l y h e x a m e t h y l e n e

p o l y a m i n e .

The

r e s i n s

a r e

d i s c l o s e d a s

b e i n g p a r t i c u l a r l y u s e f ul i n

f l e x o g r a p h i c

i n k .

A l t h o u g h t h e s e

p r o d u c t s

h a v e

g o o d s o l u b i l i t y i n

a l c o h o l

a c h i e v e d i n

p a r t

t h r o u g h

t h e c o n d e n s a t i o n

o f

a

monobasic

a c i d

a s p a r t

o f t h e a c i d

component, t h e r e s u l

t a n t l o w e r m o l e c u l a r w e i g h t p r o d u c t r e s u l t s i n l e s s

d e s i r a b l e t e n s i l e p r o p e r t i e s . S i m i l a r l y , R e . 2 8 , 5 3 3

d i s

c l o s e s s y n t h e t i c p o l y a m i d e s

p r e p a r e d

b y c o n d e n s i n g a

m o n o c a r b o x y l i c a c i d , d i a m i n e a n d d i m e r i z e d f a t t y a c i d .

A g a i n ,

t h e l o w e r

m o l e c u l a r

w e i g h t


o b

t a i n e d b y

c o n d e n s i n g

i n t e r

a l i a

a m o n o c a r b o x y l i c a c i d

20

2 5

3 0

3 5

4 5

a c h i e v e s e t h a n o l

s o l u b i l i t y

g e n e r a l l y a t t h e e x p e n s e

o f

5 0

t e n s i l e

p r o p e r t i e s .

A c c o r d i n g

t o

US.

P a t .

N o .

4 , 5 7 1 , 2 6 7 , a l c o h o l - s o l u b l e p o l y a m i d e s

a n d

p r i n t i n g i n k s

a r e d i s c l o s e d p r e p a r e d by c o n d e n s i n g

a n

a c i d

c o m p o

n e n t

of d i m e r i z e d f a t t y a c i d s ,

a t

l e a s t

one a l i p h a t i c un

branc h ed monocarboxylic a c i d and

a t

l e a s t o n e a l i p h a t i c

b r a n c h e d m o n o c a r b o x y l i c

a c i d

w i t h e t h y l e n e d i a m i n e

and h e x a m e t h y l e n e d i a m i n e a s

t h e

amine

component.

Thus t h e r e i s a

n e e d f o r p o l y a m i d e r e s i n c o m p o s i t i o n s

f o r u s e

a s

l a m i n a t i n g i n k

r e s i n

b i n d e r s

w h i c h

p o s s e s s

d e s i r a b l e

p r o p e r t i e s

s u c h

a s

good e t h a n o l s o l u b i l i t y

a n d

r e d u c i b i l i t y , g o o d v i s c o s i t y s t a b i l i t y

i n

s o l u t i o n a n d

g o o d s o f t e n i n g p o i n t s .

SUMMARY OF

THE

INVENTION

I t

h a s

been f o u n d

t h a t

i n

accordance w i t h

t h e

p r e s e n t

i n v e n t i o n a h i g h


d i a m i n e / h i g h

d i b a s i c

a c i d

p o l y a m i d e

r e s i n c o m p o s i t i o n

h a s p r o p e r t i e s e s p e '

c i a l l y

s u i t ed f o r

u s e a s a n

i n k b i n d e r

r e s i n .

More p a r t i c u

5 5

6 0

6 5

2

l a r l y i t h a s been f o u n d

t h a t

e x c e l l e n t r e s u l t s

a r e

o b t a i n e d

w i t h p o l y a m i d e r e s i n c o m p o s i t i o n s t h a t c o m p r i s e t h e

c o n d e n s a t i o n r e a c t i o n p r o d u c t o f

a

C 3 6 d i m e r i z e d f a t t y

a c i d , a t l e a s t one d i b a s i c a c i d , a t l e a s t one C1-C4 a l k y l

d i a m i n e

and

a t l e a s t

one p i p e r a z i n e - l i k e d i a m i n e , t h e

e q u i v a l e n t s o f a m i n e g r o u p s b e i n g s u b s t a n t i a l l y e q u a l t o

t h e e q u i v a l e n t s

o f c a r b o x y l

g r o u p s , where 3 0 t o 5 0

e q u i v a l e n t p e r c e n t

o f

t h e

c a r b o x y l

g r o u p s

a r e

c o n t r i b

u t e d by t h e d i b a s i c

a c i d component

a n d

7 3

t o

9 3

e q u i v a

l e n t

p e r c e n t o f

t h e amine g r o u p s a r e


by t h e

p i p e r a z i n e - l i k e d i a m i n e c o m p o n e n t .

F u r t h e r p r o v i d e d b y t h i s i n v e n t i o n i s

a

p r i n t i n g i n k

c o m p r i s i n g s o l v e n t , a p o l y a m i d e r e s i n c o m p o s i t i o n f o r

l a m i n a t i n g

i n k

r e s i n b i n d e r s i n a c c o r d a n c e w i t h

t h i s

i n v e n t i o n

and

a c o l o r a n t d i s t r i b u t e d through t h e c o m

p o s i t i o n i n an

e f f e c t i v e

am o u nt

s u f f i c i e n t

t o

i m p a r t a

p r e d e t e r m i n e d

c o l o r t o t h e r e s u l t i n g

c o m p o s i t i o n .

DETAILED

DESCRIPTION

OF

THE

PREFERRED EMBODIMENT

The

p o l y m e r i z e d f a t t y a c i d s u s e f u l i n t h e p r e s e n t

i n v e n t i o n

c a n b e

o b t a i n e d

by

t h e

p o l y m e r i z a t i o n o f

o l e ? n i c a l l y u n s a t u r a t e d m o n o c a r b o x y l i c a c i d s c o n t a i n

i n g

1 6

t o

2 3

carbon a t o m s ,

s u c h

a s o l e i c a c i d ,

l i n o l e i c

a c i d ,

l i n o l e n i c

a c i d , e l e o s t e a r i c a c i d a n d t h e

l i k e .

D i c a r

b o x y l i c a c i d s p r o d u c e d i n

t h i s

m a n n e r , t h a t i s , w h en

two m o l e s o f t h e

monocarboxylic

a c i d a r e c o m b i n e d ,

a r e r e f e r r e d t o a s dimer a c i d s . P r o c e s s e s f o r t h e produc

t i o n o f dimer a c i d s a r e w e l l kn o w n t o t h e a r t . C36 dimer

a c i d s o b t a i n e d by t h e d i m e r i z a t i o n o f a n u n s a t u r a t e d

C 1 8

a a c i d s u c h a s o l e i c a c i d ,

l i n o l e i c

a c i d and

m i x t u r e s

t h e r e o f ( e . g . t a l l o i l f a t t y a c i d s ) a r e e s p e c i a l l y u s e f u l a n d

a d v a n t a g e o u s l y

e m p l o y e d f o r t h e

p r e p a r a t i o n o f

t h e

p o l y a m i d e r e s i n c o m p o s i t i o n s

o f

t h i s i n v e n t i o n . A 3 6


a c i d

a s r e f e r r e d t o h e r e i n

r e f e r s t o

f a t t y

a c i d s

t h a t

have

a s t h e i r

p r i n c i p a l

component

a

C 3 6 d i c a r b o x y l i c

a c i d

a n d t y p i c a l l y

h a v e

a n a c i d v a l u e

i n t h e

r a n g e 1 8 0 - 2 1 5

a n d

n e u t r a l e q u i v a l e n t f r o m

2 6 5 - 3 1 0 .

C 3 6 d i m e r i z e d

f a t t y a c i d s

c o n t a i n i n g

l e s s

t h a n

30% b y w e i g h t

b y - p r o d u c t

a c i d s i n c l u d i n g m o n o b a s i c

a c i d s ,

t r i m e r

a c i d s

o r h i g h e r

polymer a c i d s a r e

e s p e

c i a l l y

u s e f u l f o r

t h i s i n v e n t i o n .

I t

i s even m o r e

advanta

g e o u s i f t h e dimer

a c i d i s

h y d r o g e n a t e d

p r i o r

t o u s e .

The d i m e r a c i d s m a y a l s o b e

m o l e c u l a r l y d i s t i l l e d o r

otherwise

puri?ed

t o

i n c r e a s e t h e C36

dimer

c o n t e n t t o

90 o r m o r e .

Another a c i d component

i n

t h e

c o n d e n s a t i o n

r e a c

t i o n

t o p r e p a r e t h e p o l y a m i d e r e s i n c o m p o s i t i o n o f t h i s

i n v e n t i o n i s

a

d i b a s i c a c i d

o r m i x t u r e of d i b a s i c

a c i d s .

C6

t o

C10

d i b a si c a c i d s

a r e b e l i e v e d

t o

b e

u s e f u l

i n t h i s

i n v e n t i o n a n d e x a m p l e s i n c l u d e a z e l a i c

a c i d ,

s e b a c i c

a c i d a n d

a d i p i c

a c i d .

C o n v e n i e n t l y ,

a z e l a i c

a c i d

i s p r e

f e r r e d . The d i b a si c a c i d s whi c h

c a n

be u s e d

i n

t h i s

i n

v e n t i o n a r e

w e l l k n o w n

i n

t h e a r t a s

i s

t h e i r

p r e p a r a t i o n

a n d many

a r e

r e a d i l y a v a i l a bl e

c o m m e r c i a l l y .

An amine c om p on e n t r e a c t a n t

i n t h i s

i n v e n t i o n i s

a

C 1 t o C4 a l k y l d i a m i n e o r m i x t u r e s

o f

C 1 t o C4 a l k y l

d i a m i n e s . The d i a m i n e s whi c h can

be

u s e d i n t h i s i n v e n

t i o n a r e w e l l k n o w n i n t h e a r t a s i s t h e i r p r e p a r a t i o n and

m a n y a r e r e a d i l y a v a i l a b l e c o m m e r c i a l l y . The s e l e c t i o n

o f

t h e

p a r t i c u l a r

d i a m i n e f o r u s e

i n

t h e p r e p a r a t i o n o f

t h e r e s i n o u s b i n d e r

o f

t h e p r e s e n t i n v e n t i o n i s d e p e n

d e n t

u p o n t h e

p r o p e r t i e s

d e s i r e d

i n

t h e c o m p o s i t i o n s o f

t h e p r e s e n t i n v e n t i o n . I t s h o u l d be a p p r e c i a t e d

t h a t

u s e

o f d i f f e r e n t

t y p e s

o f

d i a m i n e s

i n

t h e p r e p a r a t i o n

o f

t h e

r e s i n o u s b i n d e r w i l l c h a n g e t h e

v i s c o s i t y

a n d m e l t p o i n t

o f

t h e

r e s i n o u s

b i n d e r s

w h i c h

a r e

o b t a i n e d .

Conve

8/17/2019 Us 5154760

3/6

5 , 1 5 4 , 7 6 0

3

n i e n t l y , e t h y l e n e d i a m i n e (EDA) i s t h e p r e f e r r e d d i

amine i n t h i s i n v e n t i o n .

A

u r t h e r

amine component r e a c t a n t i n

t h i s i n v e n t i o n

i s a


d i a m i n e o r m i x t u r e s o f

p i p e r a z i n e

l i k e d i a m i n e s .

The

t e r m “ p i p e r a z i n e - l i k e d i a m i n e

r e f e r s

t o a

c o m p o u n d o f

t h e f o r m u l a

YNNH

he r e

Z

s

s e l e c t e d f r o m

t h e g r o u p

c o n s i s t i n g

o f

R R

R

R R

cH-i-ic CH—-HC CH-HC

a n d

nc-m-cn

R R R R R R

where R s s e l e c t e d f r o m t h e g r o u p c o n s i s t i n g o f h y d r o

gen and a l k y l

g r o u p s h a v i n g

from

1

t o

6 c a r b o n

atoms

a n d

R 1 s

a d i v a l e n t

a l i p h a t i c h y d r o c a r b o n g r o u p h a v i n g

a t l e a s t one

carbon

atom, Y s

s e l e c t e d

from

t h e gr ou p

c o n s i s t i n g

o f h y d r o g e n , R’NH; a n d R'OH where R ’ i s a

d i v a l e n t

a l k y l e n e r a d i c a l h a v i n g f r o m

1

t o 6 c a r b o n

a t o m s .

Of

t h e


d i a m i n e s , p i p e r a z i n e

i s

c o n v e n i e n t l y

p r e f e r r e d .

O t h e r


d i a m i n e s

s u c h a s a m i n o e t h y l p i p e r a z i n e a n d d i p i p e r i d y l p r o p a n e

a r e e x p e c t e d

t o

be u s e f u l . The p i p e r a z i n e - l i k e d i a m i n e s

w h i c h can be

used i n t h i s i n v e n t i o n

a r e

w e l l

k n o w n

i n

t h e

a r t a s i s t h e i r

p r e p a r a t i o n

and

m a n y a r e

r e a d i l y

a v a i l a b l e

c o m m e r c i a l l y .

The amount

of

r e a c t a n t s p r e s e n t i s e x p r e s s e d

a s

e q u i v a l e n t p e r c e n t .

G e n e r a l l y ,

3 0

t o

5 0 e q u i v a l e n t p e r

c e n t

o f t h e c a r b o x y l g r o u p s

a r e c o n t r i b u t e d by

t h e

d i b a

s i c a c i d component and

7 3

t o 9 3 e q u i v a l e n t p e r c e n t o f

t h e a m i n e

g r o u p s

a r e c o n t r i b u t e d

b y

t h e p i p e r a z i n e - l i k e

d i a m i n e c o m p o n e n t . The p o l y a m i d e

r e s i n

c o m p o s i t i o n

o f t h i s

i n v e n t i o n i s p r e p a r e d

w i t h


o f


e m p l o y e d

b e i n g

s u b s t a n t i a l l y

e q u a l

t o

t h e

e q u i v a l e n t s

o f c a r b o x y l

g r o u p s e m p l o y e d .

H o w e v e r ,

s l i g h t

e x c e s s on t h e

o r d e r o f

up t o

a b o u t

10%,

p r e f e r a

b l y

a b o u t

2 t o

a b o u t

6 , o f amine

groups a r e w i t h i n

t h e

t e r m “ s u b s t a n t i a l l y

e q u a l .

P r e f e r a b l y 3 5 t o

4 5

e q u i v a

l e n t

p e r c e n t o f t h e c a r b o x y l

g r o u p s

a r e c o n t r i b u t e d by

t h e d i b a s i c

a c i d

c o m p o n e n t , 5 5

t o

6 5 e q u i v a l e n t p e r c e n t

o f t h e c a r b o x y l g r o u p s a r e c o n t r i b u t e d by t h e d i m e r i z e d

f a t t y a c i d

component

a n d

7 8

t o

8 8

e q u i v a l e n t

p e r c e n t o f

t h e


a r e


by t h e p i p e r a z i n e - l i k e

d i a m i n e

c o m p o n e n t .

The p o l y a m i d e c o m p o s i t i o n o f

t h e

p r e s e n t

i n v e n t i o n

c a n b e

p r e p a r e d by s t a nd a r d c o n d e n s a t i o n

r e a c t i o n s

known

t o t h o s e

i n t h e

a r t . For

e x a m p l e , t h e p o l y a m i d e

c o m p o s i t i o n o f

t h e i n v e n t i o n

c a n b e p r e p a r e d

by

r e a c t

i n g

t h e a c i d c o m p o n e n t s w i t h

t h e

a m i n e c o m p o n e n t s

o p t i o n a l l y i n t h e p r e s e n c e

o f

a c a t a l y s t s u c h a s

p h o s

p h o r i c a c i d

a t

a c o n d e n s a t i o n t e m p e r a t u r e g e n e r a l l y

i n

t h e r a n g e

from

1 5 0 ° t o 2 5 0 ° C . u n t i l t h e

r e a c t i o n

i s

c o m p l e t e d . The o r d e r o f

a d d i t i o n

o f

t h e r e a c t a n t s i s n o t

c r i t i c a l .

The

p o l y a m i d e

c o m p o s i t i o n s o f t h i s

i n v e n t i o n

a r e

c h a r a c t e r i z e d b y

h a v i n g

p h y s i c a l p r o p e r t i e s

t h a t

r e n d e r

them e s p e c i a l l y u s e f u l f o r l a m i n a t i n g i n k

r e s i n

b i n d e r s .

I n

p a r t i c u l a r ,

t h e

p o l y a m i d e r e s i n c o m p o s i t i o n s o f

t h e

i n v e n t i o n h a v e

g o o d

e t h a n o l

s o l u b i l i t y

a n d


g o o d

v i s c o s i t y

s t a b i l i t y a n d g o o d s o f t e n i n g p o i n t s a s

w e l l a s

p o s s e s s i n g

o t h e r d e s i r a b l e p r o p e r t i e s .

A l s o

p r o v i d e d

by

h i s

i n v e n t i o n

i s

a p r i n t i n g i n k

c o m

p r i s i n g s o l v e n t ,

t h e

p o l y a m i d e r e s i n c o m p o s i t i o n

i n

accordance with t h i s i n v e n t i o n

and

a c o l o r a n t d i s t r i b

u t e d t h r o u g h t h e c o m p o s i t i o n i n a n e f f e c t i v e amount

4

s u f ? c i e n t

t o i m p a r t a

p r e d e t e r m i n e d

c o l o r t o t h e r e s u l t

1 5

3 5

i n g c o m p o s i t i o n .

S u i t a b l e

s o l v e n t s f o r

u s e i n t h e

m a n u f a c t u r e

o f

p r i n t

i n g i n k s a r e t h e s h o r t

c h a i n a l i p h a t i c

a l c o h o l s

h a v i n g

from 2 t o 4 carbon

atoms

w h i c h a r e

c o m m o nl y u s e d i n

t h i s

? e l d . An example

o f

a

s u i t a b l e

s o l v e n t i s e t h a n o l .

A n o t h e r i n g r e d i e n t

o f

t h e p r i n t i n g i n k o f

t h i s

i n v e n

t i o n i s t h e c o l o r a n t . The

g e n e r i c

t e r m c o l o r a n t i s

s p e c i ?

c a l l y

u s e d

i n

t h i s s p e c i ? c a t i o n i n t h a t i t i s i n t e n d e d t o

r e f e r t o b o t h

p i g m e n t s

a n d

d y e s

which i m p a r t

a d i s t i n c t

c o l o r t o t h e c o m p o s i t i o n . The p u r p o s e o f

any

c o l o r a n t

i s

t o

p r o v i d e c o n t r a s t

between t h e

c o l o r o f

t h e s u b s t r a t e

and

t h e

c o l o r o f i n k i n o r d e r

t o

p r o v i d e a v i s u a l l y i d e n t i

? a b l e

i n d i c i a on

t h e

s u b s t r a t e .

EXAMPLES

E x a m p l e

1

1 7 8 8 . 1 5

g o f c o m m e r c i a l l y a v a i l a b l e C 3 6 d i m e r i z e d

f a t t y a c i d

( 6 5

e q u i v a l e n t

p e r c e n t )

(UNIDYME

1 4 TM

l o t n o .

7 5 8 ,

s o l d

c o m m e r c i a l l y

b y U n i o n Camp

C o r p . ,

Wayne, NJ) was charged t o

a

f o u r neck

round bottom

f l a s k

? t t e d

w i t h

a

thermometer.

With

t h e

d i m e r i z e d

f a t t y

a c i d

was

a l s o c h a r g e d 3 1 6 . 5 0 g a z e l a i c

a c i d

( 3 5

e q u i v a l e n t p e r c e n t ) . The m i x t u r e was h e a t e d a n d a g i

t a t e d

u n d e r a

n i t r o g e n b l a n k e t t o a p p r o x i m a t e l y 1 0 0 ° C .

when 3 2 2 . 8 0 g p i p e r a z i n e ( 7 8 e q u i v a l e n t

p e r c e n t ) was

a d d e d f o l l o w e d

b y 7 2 . 5 5 g

e t h y l e n e d i a m i n e ( 2 5

e q u i v a _

l e n t

p e r c e n t EDA).

The m i x t u r e was

t h e n

h e a t e d

t o

1 4 0 °

C .

t o

b e g i n

l i b e r a t i n g w a t e r f r o m


r e a c t i o n . H e a t i n g was

c o n t i n u e d

u n t i l t h e r e a c t i o n mix

t u r e

r e a c h e d a p p r o x i m a t e l y

2 3 0 °

C .

The

e x t e n t

o f

t h e

r e a c t i o n was

m o n i t o r e d by

t h e a c i d number and amine

n umb e r

which were

found

t o be 7 . 7 and

1 1 . 0

r e s p e c

t i v e l y . 4 . 0 g

o f

EDA

a s

added a s an amine

c o r r e c t i o n

t o

a c h i e v e

p r o p e r

s t o i c h i o m e t r y

a n d

c o n t r o l v i s c o s i t y .

Three

drops o f

H 3 P O 4

was added a s

a

c a t a l y s t . The

r e a c t i o n

was

h e l d a t 2 3 0 °

C .

u n t i l t h e completion o f t h e

r e a c t i o n ,

about 4 h o u r s .

F i n a l l y ,

a v a c u u m of down o

6 5

mmHg

n

t h e v e s s e l

was

a p p l i e d f o r

a b o u t 2

m o r e

h o u r s

a t

23 0° C.

-

E x a m p l e 2

The

g e n e r a l

p r o c e d u r e

o f

Example

1

was f o l l o w e d

e x c e p t t h a t t h e f o l l o w i n g amounts o f

r e a c t a n t s were

e m p l o y e d

UNIDYME

4

TM

1 8 6 1 . 5 5 g

( 7 0

e q u i v a l e n t p e r c e n t )

A z e l a i c

Acid 2 6 2 . 2 5 g

( 3 0 e q u i v a l e n t p e r c e n t )

EDA 8 4 . 1 6 g


P i p e r a z i n e 2 9 2 . 0 5 g

( 7 3


_ 1 . 4

g

o f EDA was added d u r i n g t h e r e a c t i o n a s a n

amine c o r r e c t i o n .

E x a m p l e

3

The

g e n e r a l

p r o c e d u r e o f

E x a m p l e 2 w a s

f o l l o w e d

e x c e p t t h a t 6 . 0

g

o f

EDA

as added d u r i n g

t h e

r e a c t i o n

a s a n a m i n e

correction.

E x a m p l e

4

The g e n e r a l p r o c e d u r e

o f

E x a m p l e

2 was f o l l o w e d

e x c e p t t h a t 5 . 9

g

EDA a s added d u r i n g t h e r e a c t i o n a s

a n

a m i n e c o r r e c t i o n .

8/17/2019 Us 5154760

4/6

5 , 1 5 4 , 7 6 0

5

E x a m p l e

5

The g e n e r a l

p r o c e d u r e o f

Example 1 w a s f o l l o w e d

e x c e p t t h a t t h e f o l l o w i n g amounts o f r e a c t a n t s were

e m p l o y e d

UNIDYME 4

TM 1 7 6 2 . 0 7

g

( 6 2 . 9


A z e l a i c Acid 3 4 1 . 6 3 g

( 3 7 . 1


EDA 8 8 . 6 5 g

( 3 0 . 0 e q u i v a l e n t p e r c e n t )

P i p e r a z i n e

3 0 7 . 6 4 g


5 . 8

g

o f

EDA

a s

added

d u r i n g t h e r e a c t i o n

a s an


E x a m p l e 6

The

g e n e r a l p r o c e d u r e

o f Example

2

was f o l l o w e d

e x c e p t t h a t 3 . 3 g EDA as added d u r i n g

t h e r e a c t i o n

a s

an


Example

7

The g e n e r a l

p r o c e d u r e

o f E x a m p l e 2 was r e p e a t e d .

E x a m p l e

8

The

g e n e r a l

p r o c e d u r e o f Example 2 was r e p e a t e d .

E x a m p l e

9

The p r o c e d u r e o f

Example

1 was

f o l l o w e d e x c e p t

t h a t

t h e f o l l o w i n g amounts

o f

r e a c t a n t s

were employed:

UNlDYME

4 TM

1 7 0 8 . 3 3

g


A z e l a i c Acid 3 7 4 . 3 7 g


EDA 6 6 . 0 7

g


Piperazine 351.23

g


1 . 4 g of EDA

a s

added during t h e r e a c t i o n a s an


E x a m p l e 1 0

The

g e n e r a l

p r o c e d u r e

o f

Example


e x c e p t

t h a t t h e

f o l l o w i n g

amounts

of

r e a c t a n t s

were

e m p l o y e d :

UNIDYME

4

TM 1 8 2 6 . 5 0 g


A z e l a i c Acid 2 8 9 . 0 8 g


EDA 9 1 . 3 4

g

( 3 2 . 0

e q u i v a l e n t

p e r c e n t )

P i p e r a z i n e 2 9 3 . 0 9 g


E x a m p l e 1 l

The g e n e r a l p r o c e d u r e o f Example 1 was f o l l o w e d

e x c e p t t h a t

t h e

f o l l o w i n g amounts o f

r e a c t a n t s

were

e m p l o y e d :

1 O

1 5

2 0

3 5

40

.45

5 0

5 5

6

- c o n t i n u e d

A z e l a i c

Acid

3 1 6 . 4 6 g


EDA 3 1 . 4 4

g


P i p e r a z i n e 3 1 4 . 1 9 g

( 7 5 . 9


0 . 5

g of

EDA

a s

added

during

t h e r e a c t i o n a s

an


C o m p a r a t i v e E x a m p l e

A

The

g e n e r a l p r o c e d u r e o f Example 1 was

f o l l o w e d

e x c e p t t h a t t h e

f o l l o w i n g

amounts

o f


e m p l o y e d :

UNIDYME 4 TM 1 9 2 1 . 3 2

g

( 7 5


A z e l a i c Acid 2 1 0 . 5 2 g


EDA

6 7 . 5 6

g


P i p e r a z i n e

3 0 0 . 6 0

g

( 7 8


7 . 9 g of EDA a s

added

during t h e r e a c t i o n a s an


C o m p a r a t i v e

E x a m p l e

B

The

g e n e r a l p r o c e d u r e o f Example

1

was

f o l l o w e d

e x c e p t

t h a t

t h e f o l l o w i n g amounts

o f

r e a c t a n t s

were

e m p l o y e d :

UNIDYME

4 TM 1 9 3 0 . 2 2 g

( 7 5 e q u i v a l e n t

p e r c e n t )

A z e l a i c

Acid

2 1 1 . 4 9

g

( 2 5


EDA

9 5 . 0 2

g

( 3 5


P i p e r a z i n e

2 6 3 . 2 7 g


0 . 4 g of

EDA

a s

added

during t h e r e a c t i o n a s an



E x a m p l e

C

The g e n e r a l

p r o c e d u r e o f Example

1

was

f o l l o w e d

e x c e p t

t h a t

t h e f o l l o w i n g amounts o f


e m p l o y e d :

UNIDYME

4 TM

1 7 9 7 . 0 4

g


A z e l a i c Acid

3 1 8 . 0 7

g

( 3 5


EDA

10207 g


P i p e r a z i n e 2 8 2 . 8 2

g


3 . 3

g

of EDA a s

added during

t h e

r e a c t i o n

a s

an


C o m p a r a t i v e E x a m p l e D

The g e n e r a l p r o c e d u r e o f Example

1

was

f o l l o w e d

e x c e p t

t h a t t h e

f o l l o w i n g amounts

o f r e a c t a n t s

were

e m p l o y e d :

UNIDYME 4

TM

1 7 8 7 . 9 1 g

( 6 5 . 0

e q u i v a l e n t p e r c e n t ) UNIDYME 4 TM

1 9 5 1 . 4 3 g

8/17/2019 Us 5154760

5/6

5 , 1 5 4 , 7 6 0

7

- c o n t i n u e d


A z e l a i c

Acid

1 9 0 . 5 2

g

( 2 2 . 9

e q u i v a l e n t

p e r c e n t )

EDA 8 0 . 0 9 g


P i p e r a z i n e 2 7 7 . 9 5 g


5 . 8

g

of EDA

a s

added during t h e r e a c t i o n a s an



E x a m p l e

E

The

g e n e r a l


1

was f o l l o w e d

e x c e p t t h a t t h e f o l l o w i n g amounts of

r e a c t a n t s

were

e m p l o y e d :

UNIDYME 4 TM 1 8 6 7 . 8 9 g


A z e l a i c Acid 2 6 3 . 1 4

g


EDA 1 0 4 . 4 3

g

( 3 7 . 1 e q u i v a l e n t

p e r c e n t )

P i p e r a z i n e 2 6 4 . 5 4

g


4 . 3 g of EDA a s added

during

t h e r e a c t i o n a s an

a m i n e

c o r r e c t i o n .


E x a m p l e

F

The



e x c e p t

t h a t t h e f o l l o w i n g amounts

o f


employed:

UNIDYME

4

TM 1 8 5 5 . 2 5 g

( 7 0 . 0


A z e l a i c

Acid 2 6 1 . 3 6

g


EDA 6 4 . 0 2 g

( 2 2 . 9


P i p e r a z i n e 3 1 9 . 3 7

g

( 5 8 . 7


3 . 9

g of

EDA a s added during t h e r e a c t i o n

a s an

amine

c o r r e c t i o n .

C o m p a r a t i v e E x a m p l e G

The p r o c e d u r e o f

Example

1 was f o l l o w e d e x c e p t

t h a t t h e f o l l o w i n g amounts o f r e a c t a n t s were

employed:

UNIDYME

4

TM 1 8 6 3 . 9 1

g


A z e l a i c Acid 2 6 2 . 5 8 g


EDA 1 0 1 . 1 2 g

( 3 6


P i p e r a z i n e 2 7 2 . 3 9

g

( 6 8


3 . 9 g o f EDA

a s

added d u r i n g t h e

r e a c t i o n

a s

an


The

p r o p e r t i e s

a n d c h a r a c t e r i s t i c s o f

t h e v a r i o u s

p o l y a m i d e

r e s i n

c o m p o s i t i o n s a r e d e t a i l e d i n T a b l e I

1 0

20

2 5

3 5

45

5 5

8

and I I

and

elsewhere below and were

determined

f o l

l o w s :

l ) The S o f t e n i n g P o i n t

( ° C . )

was m e a s u r e d

by

c o n

v e n t i o n a l B a l l a n d

R i n g ” m e l t i n g

p o i n t

d e t e r m i n a t i o n s

ASTM D

4 6 1 - 7 6 ;

2 )

Amine

No.

i s

t h e

m i l l i g r a m s o f

KOH q u i v a l e n t

t o

a m i n e

a l k a l i n i t y

i n o n e gram s a m p l e o f c o m p o s i t i o n ;

3 ) Acid N o . i s t h e m i l l i g r a m s

o f K O l - I

e q u i v a l e n t t o

a c i d i t y

i n

o n e

gram

s a m p l e

o f

c o m p o s i t i o n ;

4 ) M e l t v i s c o s i t y ( V i s c 2 0 5 ) r e p o r t e d

i n c e n t p o i s e

( c p s ) was m e a s u r e d

b y

a d d i n g a p p r o x i m a t e l y 9 g o f

r e s i n

t o

a s a m p l e

chamber

( B r o o k ? e l d

T h e r m o c e l )

which s _

t h e n h e a t e d

t o

t h e

t e s t t e m p e r a t u r e , s u i t a b l e t o

p r o v i d e a m o l t e n

s t a t e .

A p i n d l e

( 8 0 1 - 3 )

i s

a t t a c h e d

t o

a

r o t a t i o n a l

m o t o r c a p a b l e o f

s e n s i n g

t o r q u e .

T h i s s p i n

d l e i s immersed i n t o t h e

s a m p l e

a n d

r o t a t e d

u n t i l t h e

t e m p e r a t u r e

h a s e q u i l i b r a te d ( 2 0 5 “ C . ) .

E i t h e r

a t o r q u e

f a c t o r or

a

d i r e c t r e a d o u t

m a y

be p o s s i b l e depending on

t h e model v i s c o m e t e r

( B r o o k ? e l d

R o t a t i o n a l

Viscome

t e r

model

LVT).

5 ) G a r d n e r H o l d t v i s c o s i t y o f 40% NV - p r o p a n o l

s o l u t i o n

was

measured by comparing t h e r a t e a b u b b l e

r i s e s

through

a

r e s i n

s o l u t i o n

o f

k n o w n

volume, concen

t r a t i o n

a n d t e m p e r a t u r e a g a i n s t v i s c o s i t y s t a n d a r d t u b es

i n a c o n s t a n t t e m p e r a t u r e w a t e r b a t h ( 2 5 ° C . ) . R e s u l t s

a r e c o n v e r t e d and e x p r e s s e d a s c p s ( c o n v e r s i o n t a b l e s

a l l o w t h e v i s c o s i t y r e s u l t s

t o

b e

t r e a t e d s t a t i s t i c a l l y ) .

6 )

E t h a n o l r e d u c i b i l i t y ( E t o h

R e d u c ) w a s

m e a s u r e d

a s f o l l o w s :

20

g

o f polyamide r e s i n

a r e i n t r o d u c e d i n t o

a

250 ml

Erlenmeyer

? a s k

and

d i s s o l v e d i n 3 0 g o f

n - p r o p a n o l

w i t h h e a t

a n d

a g i t a t i o n .

The s o l u t i o n i s

c o o l e d

and

p u r e

e t h y l a l c o h o l i s

t h e n

added from

a

b u r e t t e w i t h c o n s t a n t s w i r l i n g u n t i l t h e

s o l u t i o n

s t a r t s

t o

c l o u d .

E t h a n o l r e d u c i b i l i t y

i s e x p r e s s e d a s t h e p e r c e n t

o f

p o l y a m i d e r e s i n t h e n c o n t a i n e d i n

t h e

d i l u t e d ,

s t i l l

b a r e l y c l e a r

s o l u t i o n .

7 )

V i s c o s i t y s t a b i l i t y

i s

t h e G a r d n e r

v i s c o s i t y ,

a s d e

s c r i b e d a b o v e , a f t e r 7 2 h r s d i v i d e d by

t h e

i n i t i a l

Gar d

n e r

v i s c o s i t y .

8 ) F o i l a d h e s i o n i s m e a s u r e d by

m a k i n g

4 0 %

n o n

v o l a t i l e s o l u t i o n s

i n

a l c o h o l u s i n g th e

l a m i n a t i n g p o l y

a m i d e

r e s i n s . The e s i n

i s a p p l i e d t o 4X 0 i n c h p i e c e s

o f

corona t r e a t e d

aluminum

f o i l u s i n g a 4 Meyer

c o a t e d

w i r e

w o u n d

r o d and a l l o w e d t o d r y . A e n t i n e l

Heat

S e a l e r

( P a c k a g i n g

I n d u s t r i e s , H y a n n i s , MA) s

s e t

t o

200 ° F . ,

6 0 p s i

and

5

s e c o n d s . (Allow 1 5 m i n u t e s f o r

t e m p e r a t u r e t o e q u i l i b r a t e . ) A n

u n - p r i n t e d p i e c e

o f

f o i l

i s

p l a c e d on t o p

o f

a p r i n t e d

s a m p l e a n d s e a l e d i n t h e

S e n t i n e l s e a l e r . The sample i s

c u t

i n t o one

i n c h

wide

s t r i p s .

Using

a

“ T - P e e l ”

method

o f

1 2

i n c h e s

p e r m i n u t e

on

a n I n s t r o n t e s t e r

( I n s t r o n

4 2 0 1

T e s t e r ,

I n s t r o n

C o r p . ,

C a n t o n ,

MA), t h e

s a m p l e s a r e r a t e d i n grams p e r i n c h a t

m a x i m u m

l o a d .

9 )

Low t e m p e r a t u r e a d h e s i o n i s

measured

a s

de

s c r i b e d u n d e r F o i l Adhesion e x c e p t

t h a t

t h e t e m p e r a

ture o n the S e n t i n e l i s re d u ce d t o

150

“

F.

~ I n t h e f o i l a d h e s i o n t e s t s , a l l c o m p o s i t i o n s

showed

c o m p a r a b l e

p e r f o r m a n c e .

S i m i l a r l y ,

i n

t h e l o w t e m p e r

a t u r e a d h e s i o n t e s t s ,

a l l


d e m o n s t r a t e d

c o m p a r a b l e p e r f o r m a n c e i n t h a t

l a m i n a t e s

o f l l c om p o

s i t i o n s

e x h i b i t e d d e s t r u c t i v e f a i l u r e i n T - p e e l t e s t i n g on

v a r i o u s s u b s t r a t e s .

TABLE

Example No.

l 2 3 4 5 6 7 8 9 1 0 1 1

S o f t e n i n g P t .

1 2 3

1 2 0 1 2 6

1 2 9 1 3 7 1 1 5 1 2 2 1 2 5 1 2 7 1 3 1 1 2 7

8/17/2019 Us 5154760

6/6

5 , 1 5 4 , 7 6 0

9

1 0

TABLE - c o n t i n u e d

E x a m p l e N o .

l

2 3

4

5 6 7 8 9 1 O 1 1

Acid No.

2 . 0 1 . 9 1 . 5 1 . 2 1 . 9

2 . 7

1 . 8

1 . 6 1 . 0 1 . 2

1 . 7

A m i n e No.

7 . 8 5 . 4 6 . 7

6 . 2

6 . 9

6 . 8 5 . 4

7 . 4 6 . 9 7 . 2

6 . 7

V ' s c .

2 0 5 : C .

1 3 2 0 0

37250

21200 41000

27500

1 7 2 0 0 7 0 0 0 0 1 7 4 4 0 40800

28200

2 4 7 5 0

Gardner v i s e . 2 4 0 0 6 1 0 0 3 7 0 0 4 1 0 0 3 7 0 0 3 0 6 7 7 6 6 7 2 8 3 3 5 5 6 7 4 1 0 0 3 9 0 0

Etch Reduc, ‘ 7 4 2 0 . 4 2 3 . 5 2 2 . 7 2 2 . 9 2 0 . 8 2 2 . 8 2 3 . 5 2 2 . 3

1 9 . 0

2 1 . 5 2 0 . 4

Mn

2 4 4 9 2 5 0 8

3 0 3 7 2 7 6 8 3 0 4 5 4 5 6 1

3 6 7 9

2 7 9 2

3 2 9 4

1 6 9 2 2 7 7 3

MW

1 1 6 5 1 1 0 2 9 3 1 4 2 4 1 1 5 3 3 7 1 3 1 0 6 1 7 1 3 7 1 8 6 5 2 1 4 1 9 3

2 0 9 0 5

1 2 3 9 4 1 6 2 2 7

V i s e .

S t a b .

1 . 0 3 6 0 1 . 0 1 7 4 1 . 0 8 7 1 1 . 0 6 6 4 1 . 5 7 8 6 1 . 0 1 7 4 1 . 0 5 8 2 1 . 2 0 4 9 1 . 0 3 3 0 1 . 3 1 3 3 1 . 0 9 6 7

TABLE I


E x a m p l e

N o .

A B C D E F

G

S o f t e n i n g

P t .

1 0 3 1 2 1 1 3 7 1 1 2 1 3 0

1 1 1

1 3 1

Acid No.

. 9

1 . 5 1 . 6 1 . 9 3 . 0 1 . 8 1 . 1

A m i n e

No.

7 . 9

5 . 2 6 . 7

6 . 4

8 . 2 7 . 0

8 . 0

V i s e . 2 0 5

C . 1 7 7 0 0

6 7 5 0 0

5 0 5 0 0 3 3 5 0 0 6 5 2 0

22500

1 8 2 0 0

Gardner

v i s c . 2 8 3 3 6 9 3 3 5 5 6 7 5 0 3 3

1 7 3 3 3900 2950

Etch

R e d u c . , 2 4 . 5

2 4 . 0 2 4 . 4 2 5 . 4 2 1 . 6 2 2 . 9

2 1 . 9

Mn 3 1 5 1

3 4 4 9 2 7 8 4 3 6 4 1

2 1 1 8 2 1 1 2

2 2 0 4

MW 1 4 6 2 9 1 3 4 2 6 1 1 6 9 3 1 5 9 0 7 8 8 4 8 1 1 7 6 2 1 1 7 1 7

V i s c . S t a b . 0 . 9 9 3 1

1 . 0 1 7 4

2 . 0 6 5 9 0 . 9 9 4 6 1 . 7 4 7 6 1 . 3 9 6 1

1 . 6 8 8 2

W h a t

i s c l a i m e d

i s :

1 .

A

olyamide r e s i n


f o r u s e

a s

l a m i n a t

i n g

i n k

r e s i n b i n d e r w h i c h c o m p r i s e s

t h e


r e a c t i o n p r o d u c t

o f :

( a ) a C 3 6 d i m e r i z e d

f a t t y a c i d ;

( b ) a t

l e a s t one C6

t o

C10

d i b a s i c

a c i d ; ( 0 ) a t

l e a s t

one C1-C4

a l k y l d i a m i n e ;

a n d ( d ) a t l e a s t

o n e p i p e r a z i n e - l i k e

d i

a m i n e ;

t h e e q u i v a l e n t s o f a m i n e g r o u p s b e i n g

s u b s t a n

t i a l l y e q u a l t o t h e


o f c a r b o x y l g r o u p s ,

where 3 5 t o

4 5

e q u i v a l e n t

p e r c e n t o f t h e c a r b o x y l

g r o u p s a r e

c o n t r i b u t e d by

t h e

d i b a si c a c i d component,

5 5 t o 6 5 e q u i v a l e n t p e r c e n t o f t h e c a r b o x y l g r o u p s a r e

c o n t r i b u t e d by

t h e


a c i d

component

a n d

7 8

t o 8 8


o f

t h e

amine

g r o u p s

a r e


b y

t h e p i p e r a z i n e - l i k e d i a m i n e c o m p o n e n t .

2 . The

p o l y a m i d e

r e s i n

c o m p o s i t i o n a c c o r d i n g

t o

c l a i m 1

t h e

d i b a s i c a c i d i s a z e l a i c a c i d .

3 .

The

p o l y a m i d e

r e s i n

c o m p o s i t i o n a c c o r d i n g

t o

c l a i m 1

w h e r e i n

t h e p i p e r a z i n e - l i k e d i a m i n e i s p i p e r a

zine.

4 . The

p o l y a m i d e

r e s i n

c o m p o s i t i o n a c c o r d i n g t o

c l a i m

1

w h e r e i n

t h e

C 1

t o

C4 l k y l d i a m i n e s

e t h y l e n e d i

a m i n e .

5 .

A

olyamide r e s i n


f o r u s e a s

l a m i n a t

i n g i n k r e s i n b i n d e r

w h i c h c o m p r i s e s


r e a c t i o n p r o d u c t o f : ( a )

a b o u t

6 0 e q u i v a l e n t p e r c e n t o f a

C 3 6 d i m e r i z e d f a t t y a c i d ; ( b ) a b o u t

4 0


a z e l a i c

a c i d ;

( c )

e t h y l e n e d i a m j n e

i n

a n

amount

s u f f i c i e n t

t o

p r o v i d e

a b o u t 2 t o a b o u t 6 e q u i v a l e n t p e r c e n t e x c e s s

o f

a m i n e g r o u p s ;

a n d ( d )

a b o u t 8 3 e q u i v a l e n t

p e r c e n t

p i p e r a z i n e .

6 . A r i n t i n g i n k c o m p r i s i n g :

( a )

a

C2-C4

a l i p h a t i c

a l c o h o l

s o l v e n t , ( b ) a p o l y a m i d e

r e s i n


w h i c h c o m p r i s e s t h e


r e a c t i o n p r o d u c t o f :

( a )

a

C 3 6 d i m e r i z e d f a t t y a c i d ; ( b ) a t l e a s t

o n e

C6

t o C 1 0

d i b a s i c

a c i d ; ( 0 ) a t l e a s t

o n e C1-C4 a l k y l

d i a m i n e ; a n d

( d ) a t

l e a s t

o n e


d i a m i n e ;


o f

a m i n e

g r o u p s

b e i n g s u b s t a n t i a l l y

e q u a l t o

t h e

e q u i v a

l e n t s o f c a r b o x y l g r o u p s , where 3 0

t o

5 0 e q u i v a l e n t

p e r c e n t

o f

t h e c a r b o x y l

g r o u p s

a r e


by t h e


component

a n d 7 3 t o 9 3 e q u i v a l e n t p e r c e n t

o f t h e amine g r o u p s a r e c o n t r i b u t e d by t h e

p i p e r a z i n e

l i k e d i a m i n e

component, and

( c ) a c o l o r a n t d i s t r i b u t e d

t h r o u g h t h e


i n a n e f f e c t i v e

amount s u f f r

c i e n t

t o i m p a r t

a c o l o r

t o

t h e r e s u l t i n g

p r i n t i n g i n k .

7 .

The p r i n t i n g i n k a c c o r d i n g t o

c l a i m

6

w h e r e i n

t h e


i s a z e l a i c

a c i d .

2 5

45

5 0

5 5

6 5

8 .

The p r i n t i n g i n k a c c o r d i n g t o

c l a i m

6 w h e r e i n t h e

p i p e r a z i n e - l i k e d i a m i n e

i s


9 .

The p r i n t i n g

i n k

a c c o r d i n g t o

c l a i m 6

w h e r e i n t h e

C 1 t o

C4

l k y l d i a m i n e

i s e t h y l e n e d i a m i n e .

1 0 . A

r i n t i n g i n k

c o m p r i s i n g :

a n

a l c o h o l

s o l v e n t ,

a p o l y a m i d e r e s i n

c o m p o s i t i o n w h i c h c o m p r i s e s

t h e

c o n d e n s a t i o n r e a c t i o n

p r o d u c t o f : ( a )

a C 3 6 d i m e r

i z e d

f a t t y a c i d ; ( b ) a t l e a s t

o n e

C6 t o

C 1 0 d i b a s i c

a c i d ;

( 0 ) a t

l e a s t o n e

C1-C4

l k y l

d i a m i n e ; a n d ( d ) a t

l e a s t

o n e p i p e r a z i n e - l i k e d i a m i n e ; t h e e q u i v a l e n t s

o f

a m i n e g r o u p s b e i n g s u b s t a n t i a l l y

e q u a l

t o t h e


o f c a r b o x y l

g r o u p s ,

where

3 5

t o

4 5

e q u i v a l e n t

p e r c e n t o f t h e

c a r b o x y l

g r o u p s a r e con

t r i b u t e d

by t h e d i b a s i c a c i d

c o m p o n e n t , 5 5 t o

6 5

e q u i v a l e n t p e r c e n t o f t h e c a r b o x y l

g r o u p s

a r e

con

t r i b u t e d by t h e d i m e r i z e d f a t t y a c i d

component

a n d

7 8

t o

8 8 e q u i v a l e n t p e r c e n t

o f

t h e amine groups a r e


b y t h e p i p e r a z i n e - l i k e d i a m i n e

compo

n e n t ,

and

a

c o l o r a n t

d i s t r i b u t e d t h r o u g h

t h e

p r i n t i n g i n k i n a n

e f f e c t i v e am o u nt s u f f i c i e n t t o impart a c o l o r t o t h e

r e s u l t i n g

p r i n t i n g

i n k .

1 1 .

The


a c c o r d i n g

t o c l a i m 1 0 w h e r e i n

t h e


i s

a z e l a i c a c i d .

1 2 . The p r i n t i ng i n k a c c o r d i n g t o c l a i m 1 0 w h e r e i n

t h e


d i a m i n e

i s


1 3 .

The

p r i n t i n g

i n k

a c c o r d i n g

t o c l a i m 1 0

w h e r e i n

t h e C 1

t o

C4

l k y l

d i a m i n e i s e t h y l e n e d i a m i n e .

1 4 .

The

p r i n t i n g

i n k

a c c o r d i n g

t o

c l a i m

1 0 w h e r e i n

t h e a l c o h o l s o l v e n t i s

c o m p r i s e d

p r i m a r i l y

o f

a

C2-C4

aliphatic alcohol.

1 5 .

A

r i n t i n g i n k c o m p r i s i n g :

a C2-C4 l i p h a t i c

a l c o h o l

s o l v e n t ,

a

p o l y a m i d e

r e s i n


w h i c h

c o m p r i s e s

t h e


r e a c t i o n p r o d u c t

o f : ( a ) a b o u t 6 0


o f

a C 3 6 d i m e r i z e d

f a t t y a c i d ;

( b )

a b o u t

4 0


a z e l a i c

a c i d ; ( c ) e t h y l

enediamine

i n

an

am o u nt

s u f f i c i e n t

t o

provide

a b o u t 2 t o a b o u t 6 e q u i v a l e n t p e r c e n t e x c e s s o f

a m i n e

g r o u p s ;

a n d

1 )

a b o u t

8 3


p i p e r a z i n e , a n d

a

c o l o r a n t

d i s t r i b u t e d

through t h e

p r i n t i n g i n k i n a n

e f f e c t i v e am o u nt s u f f i c i e n t t o impart

a

c o l o r t o

t h e

r e s u l t i n g

p r i n t i n g

i n k .

t t i i i t

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